HCl to pH 2C3

HCl to pH 2C3. DMSO mainly because positive and negative settings, respectively. The same quantity (50 L) of diluted cells was put into the plates using the serial medication dilution. Plates had been covered in Ziplock hand bags and incubated at 37 C. After 7C14 times, plates had been examine with an enlarging inverted reflection plate reader. The MIC was recorded as the concentration that inhibited all visible growth fully. 3.4. In Vitro Cytotoxicity Assay The cytotoxicity of substances on MRC-5 fibroblasts was performed just as previously reported [14]. 3.5. Chemistry All solvents and reagents were purchased from regular business resources and were of analytical quality. All synthetic substances described with this research had been examined with analytical TLC (Macherey?Nagel precoated F254 light weight aluminum plates, Dren, Germany), visualized under UV light in 254 nm and purified by column chromatography (CC) on the Reveleris X2 (Elegance, BCHI, Flawil, Switzerland) automated adobe flash unit. All last compounds plus some intermediates had been assessed with Varian Mercury 300/75 MHz (Palo Alto, CA, USA) or a Bruker AVANCE (F?llanden, Zrich, Switzerland) Neo? 400/100 MHz spectrometer at 298.15 K using tetramethylsilane (TMS) as an interior standard. The verification and evaluation of the ultimate substances had been carried out with 1H, 13C, HSQC and HMBC NMR spectral data (Supplementary Components). High-resolution mass spectrometry was performed on the Waters LCT Leading XETM (Waters, Zellik, Belgium) time-of-flight (TOF) mass spectrometer built with a typical electrospray ionization (ESI) and modular LockSprayTM user interface (Waters, Zellik, Belgium). The purity from the examined compounds was dependant on LC-MS analysis utilizing a Waters AutoPurification program built with a Waters Cortecs C18 column (2.7 m, 100 4.6 mm), as was a gradient program of formic acidity in H2O (0.2%, (6). To a remedy of methyl 2-([1,1-biphenyl]-4-yl)acetate (0.3 g, 1.3 mmol) in dried out THF (7.8 mL) was added LiAlH4 (0.10 g, 2.7 mmol) to provide alcohol intermediate, that was oxidized with PCC (0.56 g, 2.6 mmol) in DCM (13.0 mL) to produce aldehyde 6 (C14H12O, 0.22 g, 1.1 mmol). (12a). Following a general treatment A, methyl 2-(2-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(2-phenoxyphenyl)acetate 10a (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.40 g, 1.6 mmol, 21% produce). 1H NMR (300 MHz, CDCl3) ppm 3.63 (s, 3 H, OCH3), 3.72 (s, 2 H, CH2), 6.90 (dd, = 8.1, 1.0 Hz, 1 H, Ph), 6.95C7.01 (m, 2 H, Ph), 7.06C7.15 (m, 2 H, Ph), 7.21C7.37 (m, 4 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 35.6 (1 C, CH2), 51.8 (1 C, OCH3), 118.3 (2 C, Ph), 118.8 (1 C, Ph), 123.0 (1 C, Ph), 123.6 (1 C, Ph), 125.8 (1 C, Ph), 128.6 (1 C, Ph), 129.6 (2 C, Ph), 131.4 (1 C, Ph), 155.0 (1 C, Ph), 157.2 (1 C, Ph), 171.7 (1 C, CO). After that, 10a (0.20 g, 0.83 mmol) was treated with LiAlH4 (63 mg, 1.7 mmol) in dried out THF (5.0 mL) to provide alcohol intermediate, that was oxidized with PCC (0.34 g, 1.6 mmol) in DCM (8.0 mL) to produce aldehyde 12a (C14H12O2, 0.15 g, 0.70 mmol). (12b). Following a general treatment A, methyl 2-(3-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(3-phenoxyphenyl)acetate 10b (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.80 g, 3.3 mmol, 41% produce). 1H NMR (300 MHz, CDCl3) ppm 3.62 (s, 2 H, CH2), 3.71 (s, 3 H, OCH3), 6.90 – 6.95 (m, 1 H, Ph), 6.98 (t, = 2.1 Hz, 1.Pursuing ppm 1.64 (d, = 10.6 Hz, 2 H, piperdyl-3a-yl, piperidyl-5a-yl), 1.73 – 1.87 (m, 5 H, 5-CH3, piperdyl-3b-yl, piperidyl-5b-yl), 2.05 (t, = 11.1 Hz, 2 H, piperidyl-2a-yl, piperidyl-6a-yl), 2.28 (s, 3 H, PhCH3), 2.54 (d, = 8.4 Hz, 2 H, CH2N), 2.72 (t, = 7.5 Hz, 2 H, PhCH2), 3.02 (d, = 11.5 Hz, Picaridin 2 H, piperidyl-2b-yl, piperidyl-6b-yl), 4.19C4.29 (m, 1 H, piperidyl-4-yl), 6.77 (d, = 8.1 Hz, 1 H, Ph), 6.87 (s, 1 H, Ph), 6.90 (d, = 8.3 Hz, 2 H, Ph), 6.98 (d, = 7.6 Hz, 1 H, Ph), 7.19 (d, = 8.4 Hz, 2 H, Ph), 7.26 (t, = 7.8 Hz, 1 H, Ph), 7.61 (s, 1 H, H-6), 11.20 (s, 1 H, NH). After 7C14 times, plates had been browse with an enlarging inverted reflection plate audience. The MIC was documented as the focus that completely inhibited all noticeable development. 3.4. In Vitro Cytotoxicity Assay The cytotoxicity of substances on MRC-5 fibroblasts was performed just as previously reported [14]. 3.5. Chemistry All reagents and solvents had been purchased from regular commercial resources and had been of analytical quality. All synthetic substances described within this research had been examined with analytical TLC (Macherey?Nagel precoated F254 lightweight aluminum plates, Dren, Germany), visualized under UV light in 254 nm and purified by column chromatography (CC) on the Reveleris X2 (Sophistication, BCHI, Flawil, Switzerland) automated display unit. All last compounds plus some intermediates had been assessed with Varian Mercury 300/75 MHz (Palo Alto, CA, USA) or a Bruker AVANCE (F?llanden, Zrich, Switzerland) Neo? 400/100 MHz spectrometer at 298.15 K using tetramethylsilane (TMS) as an interior standard. The evaluation and verification of the ultimate compounds had been executed with 1H, 13C, HSQC and HMBC NMR spectral data (Supplementary Components). High-resolution mass spectrometry was performed on the Waters LCT Top XETM (Waters, Zellik, Belgium) time-of-flight (TOF) mass spectrometer built with a typical electrospray ionization (ESI) and modular LockSprayTM user interface (Waters, Zellik, Belgium). The purity from the examined compounds was dependant on LC-MS analysis utilizing a Waters AutoPurification program built with a Waters Cortecs C18 column (2.7 m, 100 4.6 mm), as was a gradient program of formic acidity in H2O (0.2%, (6). To a remedy of methyl 2-([1,1-biphenyl]-4-yl)acetate (0.3 g, 1.3 mmol) in dried out THF (7.8 mL) was added LiAlH4 (0.10 g, 2.7 mmol) to provide alcohol intermediate, that was oxidized with PCC (0.56 g, 2.6 mmol) in DCM (13.0 mL) to produce aldehyde 6 (C14H12O, 0.22 g, 1.1 mmol). (12a). Following general method A, methyl 2-(2-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(2-phenoxyphenyl)acetate 10a (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.40 g, 1.6 mmol, 21% produce). 1H NMR (300 MHz, CDCl3) ppm 3.63 (s, 3 H, OCH3), 3.72 (s, 2 H, CH2), 6.90 (dd, = 8.1, 1.0 Hz, 1 H, Ph), 6.95C7.01 (m, 2 H, Ph), 7.06C7.15 (m, 2 H, Ph), 7.21C7.37 (m, 4 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 35.6 (1 C, CH2), 51.8 (1 C, OCH3), 118.3 (2 C, Ph), 118.8 (1 C, Ph), 123.0 (1 C, Ph), 123.6 (1 C, Ph), 125.8 (1 C, Ph), 128.6 (1 C, Ph), 129.6 (2 C, Ph), 131.4 (1 C, Ph), 155.0 (1 C, Ph), 157.2 (1 C, Ph), 171.7 (1 C, CO). After that, 10a (0.20 g, 0.83 mmol) was treated with LiAlH4 (63 mg, 1.7 mmol) in dried out THF (5.0 mL) to provide alcohol intermediate, that was oxidized with PCC (0.34 g, 1.6 mmol) in DCM (8.0 mL) to produce aldehyde 12a (C14H12O2, 0.15 g, 0.70 mmol). (12b). Following general method A, methyl 2-(3-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(3-phenoxyphenyl)acetate 10b (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.80 g, 3.3 mmol, 41% produce). 1H NMR (300 MHz, CDCl3) ppm 3.62 (s, 2 H, CH2), 3.71 (s, 3 H, OCH3), 6.90 – 6.95 (m, 1 H, Ph), 6.98 (t, = 2.1 Hz, 1 H, Ph), 7.01C7.07 (m, 3 H, Ph), 7.13 (tt, = 7.4, 1.1 Hz, 1 H, Ph), 7.26C7.40.Pursuing ppm 1.79 (s, 3 H, 5-CH3), 2.00 (d, = 12.0 Hz, 2 H, piperdyl-3a-yl, piperidyl-5a-yl), 2.20 (d, = 11.4 Hz, 2 H, piperdyl-3b-yl, piperidyl-5b-yl), 2.99 – 3.08 (m, 2 H, PhCH2), 3.16 (d, = 9.5 Hz, 2 H, piperidyl-2a-yl, piperidyl-6a-yl), 3.39C3.55 (m, 2 H, CH2N), 3.67 (d, = 10.6 Hz, 2 H, piperidyl-2b-yl, piperidyl-6b-yl), 4.47C4.59 (m, 1 H, piperidyl-4-yl), 7.05 (d, = 7.9 Hz, 1 H, Ph), 7.10C7.20 (m, 4 H, Ph), 7.39 (br. had been browse with an enlarging inverted reflection plate audience. The MIC was documented as the focus that completely inhibited all noticeable development. 3.4. In Vitro Cytotoxicity Assay The cytotoxicity of substances on MRC-5 fibroblasts was performed just as previously reported [14]. 3.5. Chemistry All reagents and solvents had been purchased from regular commercial resources and had been of analytical quality. All synthetic substances described within this research had been examined with analytical TLC (Macherey?Nagel precoated F254 lightweight aluminum plates, Dren, Germany), visualized under UV light in 254 nm and purified by column chromatography (CC) on the Reveleris X2 (Sophistication, BCHI, Flawil, Switzerland) automated display unit. All last compounds plus some intermediates had been assessed with Varian Mercury 300/75 MHz (Palo Alto, CA, USA) or a Bruker AVANCE (F?llanden, Zrich, Switzerland) Neo? 400/100 MHz spectrometer at 298.15 K using tetramethylsilane (TMS) as an interior standard. The evaluation and verification of the ultimate compounds had been executed with 1H, 13C, HSQC and HMBC NMR spectral data (Supplementary Components). High-resolution mass spectrometry was performed on the Waters LCT Top XETM (Waters, Zellik, Belgium) time-of-flight (TOF) mass spectrometer built with a typical electrospray ionization (ESI) and modular LockSprayTM user interface (Waters, Zellik, Belgium). The purity from the examined compounds was dependant on LC-MS analysis utilizing a Waters AutoPurification program built with a Waters Cortecs C18 column (2.7 m, 100 4.6 mm), as was a gradient program of formic acidity in H2O (0.2%, (6). To a remedy of methyl 2-([1,1-biphenyl]-4-yl)acetate (0.3 g, 1.3 mmol) in dried out THF (7.8 mL) was added LiAlH4 (0.10 g, 2.7 mmol) to provide alcohol intermediate, that was oxidized with PCC (0.56 g, 2.6 mmol) in DCM (13.0 mL) to produce aldehyde 6 (C14H12O, 0.22 g, 1.1 mmol). (12a). Following general method A, methyl 2-(2-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(2-phenoxyphenyl)acetate 10a (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.40 g, 1.6 mmol, 21% produce). 1H NMR (300 MHz, CDCl3) ppm 3.63 (s, 3 H, OCH3), 3.72 (s, 2 H, CH2), 6.90 (dd, = 8.1, 1.0 Hz, 1 H, Ph), 6.95C7.01 (m, 2 H, Ph), 7.06C7.15 (m, 2 H, Ph), 7.21C7.37 (m, 4 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 35.6 (1 C, CH2), 51.8 (1 C, OCH3), 118.3 (2 C, Ph), 118.8 (1 C, Ph), 123.0 (1 C, Ph), 123.6 (1 C, Ph), 125.8 (1 C, Ph), 128.6 (1 C, Ph), 129.6 (2 C, Ph), 131.4 (1 C, Ph), 155.0 (1 C, Ph), 157.2 (1 C, Ph), 171.7 (1 C, CO). After that, 10a (0.20 g, 0.83 mmol) was treated with LiAlH4 (63 mg, 1.7 mmol) in dried out THF (5.0 mL) to provide alcohol intermediate, that was oxidized with PCC (0.34 g, 1.6 mmol) in DCM (8.0 mL) to produce aldehyde 12a (C14H12O2, 0.15 g, 0.70 mmol). (12b). Following general method A, methyl 2-(3-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 Picaridin g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(3-phenoxyphenyl)acetate 10b (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.80 g, 3.3 mmol, 41% produce). 1H.13C NMR (75 MHz, CDCl3) ppm 40.9 (1 C, CH2), 52.0 (1 C, OCH3), 117.3 (1 C, Ph), 119.0 (2 C, Ph), 119.7 (1 C, Ph), 123.3 (1 C, Ph), 124.0 (1 C, Ph), 129.7 (3 C, Ph), 135.7 (1 C, Ph), 156.9 (1 C, Ph), 157.4 (1 C, Ph), 171.6 (1 C, CO). within a focus range spanning 100-0.049 M in sterile 96-well U-bottom clear polystyrene microtiter plates. DMSO and Isoniazid as negative and positive handles, respectively. The same quantity (50 L) of diluted cells was put into the plates using the serial medication dilution. Plates had been covered in Ziplock luggage and incubated at 37 C. After 7C14 times, plates had been browse with an enlarging inverted reflection plate audience. The MIC was documented as the focus that completely inhibited all noticeable development. 3.4. In Vitro Cytotoxicity Assay The cytotoxicity of substances on MRC-5 fibroblasts was performed just as previously reported [14]. 3.5. Chemistry All reagents and solvents had been purchased from regular commercial resources and had been of analytical quality. All synthetic substances described within this research had been examined with analytical TLC (Macherey?Nagel precoated F254 lightweight aluminum plates, Dren, Germany), visualized under UV light in 254 nm and purified by column chromatography (CC) on the Reveleris X2 (Sophistication, BCHI, Flawil, Switzerland) automated display unit. All last compounds plus some intermediates had been assessed with Varian Mercury 300/75 MHz (Palo Alto, CA, USA) or a Bruker AVANCE (F?llanden, Zrich, Switzerland) Neo? 400/100 MHz spectrometer at 298.15 K using tetramethylsilane (TMS) as an interior standard. The evaluation and verification of the ultimate compounds had been executed with 1H, 13C, HSQC and HMBC NMR spectral data (Supplementary Components). High-resolution mass spectrometry was performed Picaridin on the Waters LCT Top XETM (Waters, Zellik, Belgium) time-of-flight (TOF) mass spectrometer built with a typical electrospray ionization (ESI) and modular LockSprayTM user interface (Waters, Zellik, Belgium). The purity from the examined compounds was dependant on LC-MS analysis utilizing a Waters AutoPurification program built with a Waters Cortecs C18 column (2.7 m, 100 4.6 mm), as was Picaridin a gradient program of formic acidity in H2O (0.2%, (6). To a remedy of methyl 2-([1,1-biphenyl]-4-yl)acetate (0.3 g, 1.3 mmol) in dried out THF (7.8 mL) was added LiAlH4 (0.10 g, 2.7 mmol) to provide alcohol intermediate, that was oxidized with PCC (0.56 g, 2.6 mmol) in DCM (13.0 mL) to produce aldehyde 6 (C14H12O, 0.22 g, 1.1 mmol). (12a). Following general method A, methyl 2-(2-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(2-phenoxyphenyl)acetate 10a (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.40 g, 1.6 mmol, 21% produce). 1H NMR (300 MHz, CDCl3) ppm 3.63 (s, 3 H, OCH3), 3.72 (s, 2 H, CH2), 6.90 (dd, = 8.1, 1.0 Hz, 1 H, Ph), 6.95C7.01 (m, 2 H, Ph), 7.06C7.15 (m, 2 H, Ph), 7.21C7.37 (m, 4 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 35.6 (1 C, CH2), 51.8 (1 C, OCH3), 118.3 (2 C, Ph), 118.8 (1 C, Ph), 123.0 (1 C, Ph), 123.6 (1 C, Ph), 125.8 (1 C, Ph), 128.6 (1 C, Ph), 129.6 (2 C, Ph), 131.4 (1 C, Ph), 155.0 (1 C, Ph), 157.2 (1 C, Ph), 171.7 (1 C, CO). After that, 10a (0.20 g, 0.83 mmol) was treated with LiAlH4 (63 mg, 1.7 mmol) in dried out THF (5.0 mL) to provide alcohol intermediate, that was oxidized with PCC (0.34 g, 1.6 mmol) in DCM (8.0 mL) to produce aldehyde 12a (C14H12O2, 0.15 g, 0.70 mmol). (12b). Following general method A, methyl 2-(3-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(3-phenoxyphenyl)acetate 10b (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.80 g, 3.3 mmol, 41% produce). 1H NMR (300 MHz, CDCl3) ppm 3.62 (s, 2 H, CH2), 3.71 (s, 3 H, OCH3), 6.90 – 6.95 (m, 1 H, Ph), 6.98 (t, = 2.1 Hz, 1 H, Ph), 7.01C7.07 (m, 3 H, Ph), 7.13 (tt, = 7.4, 1.1 Hz, 1 H, Ph), 7.26C7.40 (m, 3 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 40.9 (1 C, CH2), 52.0 (1 C, OCH3), 117.3 (1 C, Ph), 119.0 (2 C, Ph), 119.7 (1 C, Ph), 123.3 (1 C, Ph), 124.0 (1 C, Ph), 129.7 (3 C, Ph), 135.7 (1 C, Ph), 156.9 (1 C, Ph), 157.4 (1 C, Ph), 171.6 (1 C, CO). After that, 10b (0.20 g, 0.83 mmol) was treated with LiAlH4 (63 mg, 1.7 mmol) in dried out THF (5.0 mL) to provide alcohol intermediate, that was oxidized with.for [C24H25Cl2N3O3 + H]+ 474.1346, found 474.1333. (21h). 37 C. After 7C14 times, plates had been browse with an enlarging inverted reflection plate audience. The MIC was documented as the focus that completely inhibited all noticeable development. 3.4. In Vitro Cytotoxicity Assay The cytotoxicity of substances on MRC-5 fibroblasts was performed just as previously reported [14]. 3.5. Chemistry All reagents and solvents had been purchased from regular commercial resources and had been of analytical quality. All synthetic substances described within this research had been examined with analytical TLC (Macherey?Nagel precoated F254 light weight aluminum plates, Dren, Germany), visualized under UV light in 254 nm and purified by column chromatography (CC) on the Reveleris X2 (Sophistication, BCHI, Flawil, Switzerland) automated display unit. All last compounds plus some intermediates had been assessed with Varian Mercury 300/75 MHz (Palo Alto, CA, USA) or a Bruker AVANCE (F?llanden, Zrich, Switzerland) Neo? 400/100 MHz spectrometer at 298.15 K using tetramethylsilane (TMS) as an interior standard. The evaluation and verification of the ultimate compounds had been executed with 1H, 13C, HSQC and HMBC NMR spectral data (Supplementary Components). High-resolution mass spectrometry was performed on the Waters LCT Top XETM (Waters, Zellik, Belgium) time-of-flight CASP9 (TOF) mass spectrometer built with a typical electrospray ionization (ESI) and modular LockSprayTM user interface (Waters, Zellik, Belgium). The purity from the examined compounds was dependant on LC-MS analysis utilizing a Waters AutoPurification program built with a Waters Cortecs C18 column (2.7 m, 100 4.6 mm), as was a gradient program of formic acidity in H2O (0.2%, (6). To a remedy of methyl 2-([1,1-biphenyl]-4-yl)acetate (0.3 g, 1.3 mmol) in dried out THF (7.8 mL) was added LiAlH4 (0.10 g, 2.7 mmol) to provide alcohol intermediate, that was oxidized with PCC (0.56 g, 2.6 mmol) in DCM (13.0 mL) to produce aldehyde 6 (C14H12O, 0.22 g, 1.1 mmol). (12a). Following general treatment A, methyl 2-(2-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(2-phenoxyphenyl)acetate 10a (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.40 g, 1.6 mmol, 21% produce). 1H NMR (300 MHz, CDCl3) ppm 3.63 (s, 3 H, OCH3), 3.72 (s, 2 H, CH2), 6.90 (dd, = 8.1, 1.0 Hz, 1 H, Ph), 6.95C7.01 (m, 2 H, Ph), 7.06C7.15 (m, 2 H, Ph), 7.21C7.37 (m, 4 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 35.6 (1 C, CH2), 51.8 (1 C, OCH3), 118.3 (2 C, Ph), 118.8 (1 C, Ph), 123.0 (1 C, Ph), 123.6 (1 C, Ph), 125.8 (1 C, Ph), 128.6 (1 C, Ph), 129.6 (2 C, Ph), 131.4 (1 C, Ph), 155.0 (1 C, Ph), 157.2 (1 C, Ph), 171.7 (1 C, CO). After that, 10a (0.20 g, 0.83 mmol) was treated with LiAlH4 (63 mg, 1.7 mmol) in dried out THF (5.0 mL) to provide alcohol intermediate, that was oxidized with PCC (0.34 g, 1.6 mmol) in DCM (8.0 mL) to produce aldehyde 12a (C14H12O2, 0.15 g, 0.70 mmol). (12b). Following general treatment A, methyl 2-(3-hydroxyphenyl)acetate (1.1 g, 8.1 mmol), phenylboronic acidity (2.9 g, 24 mmol), Cu(OAc)2 (2.9 g, 16 mmol), 4? molecular sieves (1.5 g) and pyridine (1.9 mL, 24 mmol) in 1,2-dichloroethane (49 mL) afforded the ester intermediate methyl 2-(3-phenoxyphenyl)acetate 10b (eluent system: 10% ethylacetate in petroleum ether, C15H14O3, 0.80 g, 3.3 mmol, 41% produce). 1H NMR (300 MHz, CDCl3) ppm 3.62 (s, 2 H, CH2), 3.71 (s, 3 H, OCH3), 6.90 – 6.95 (m, 1 H, Ph), 6.98 (t, = 2.1 Hz, 1 H, Ph), 7.01C7.07 (m, 3 H, Ph), 7.13 (tt, = 7.4, 1.1 Hz, 1 H, Ph), 7.26C7.40 (m, 3 H, Ph). 13C NMR (75 MHz, CDCl3) ppm 40.9 (1 C, CH2), 52.0 (1 C, OCH3), 117.3 (1 C, Ph), 119.0 (2 C, Ph), 119.7 (1 C, Ph), 123.3 (1 C, Ph), 124.0 (1 C, Ph), 129.7 (3 C, Ph), 135.7 (1 C, Ph), 156.9 (1 C, Ph), 157.4 (1 C, Ph), 171.6 (1 C, CO). After that,.