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With triethylamine In dichloromethane at 20℃; Cooling with ice
Intermediate 71{(S)-6-[(R)-4-(5-Hvdroxy-2-methyl-phenyl)-indan-1 -yloxy1-2,3-dihydro-benzofuran-3- yl)-acetic acid methyl esterStep 1 : (3-bromo-4-methyl-phenoxy)-tert-butyl-dimethyl-silane tert-Butyldimethylsilyl chloride (0.18 g) is added to a solution of 3-bromo-4-methyl- phenol (0.20 g) and triethylamine (0.23 ml_) in dichloromethane (3 ml_) chilled in an ice bath. 4-Dimethylaminopyridine (13 mg) is added and the solution is stirred at room temperature overnight. Dichloromethane is added and the solution is washed with 1 M hydrochloric acid, aqueous NaHC03 solution, and brine, and dried (MgS04). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. Yield: 0.25 g (78percent of theory); LC (method 1 ): tR = 1 .59 min.
78%
With dmap; triethylamine In dichloromethane at 20℃; Cooling with ice
Intermediate 71{(S)-6-[(R)-4-(5-Hydroxy-2-methyl-phenyl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester Step 1: (3-bromo-4-methyl-phenoxy)-tert-butyl-dimethyl-silanetert-Butyldimethylsilyl chloride (0.18 g) is added to a solution of 3-bromo-4-methyl-phenol (0.20 g) and triethylamine (0.23 mL) in dichloromethane (3 mL) chilled in an ice bath. 4-Dimethylaminopyridine (13 mg) is added and the solution is stirred at room temperature overnight. Dichloromethane is added and the solution is washed with 1 M hydrochloric acid, aqueous NaHCO3 solution, and brine, and dried (MgSO4).The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. Yield: 0.25 g (78percent of theory); LC (method 1): tR=1.59 min.
With 1H-imidazole; In dichloromethane; at 20℃; for 3h;
General procedure: Add TBSCl (3.37 g, 22.37 mmol) and imidazole (1.9 g, 27.96 mmol) to a solution of 3-bromo-4-fluoro-phenol (3.56 g 18.64 mmol) in CH2Cl2 (60 ml). Stir the solution at ambient temperature for 3 hours. Quench the reaction with water (30 mL). Extract the aqueous layer with CH2Cl2 (30 mL×3). The combined organic layers are washed with brine, dried over Na2SO4, concentrated under vacuum. The residue is purified by silica gel chromatography (petroleum ether) to give (3-bromo-4-fluoro-phenoxy)-tert-butyl-dimethyl-silane as colorless oil (5.81 g, 99%), MS (m/z): 303 (M-1).
With triethylamine;dmap; In dichloromethane; at 20℃;Cooling with ice;
Intermediate 71{(S)-6-[(R)-4-(5-Hvdroxy-2-methyl-phenyl)-indan-1 -yloxy1-2,3-dihydro-benzofuran-3- yl)-acetic acid methyl esterStep 1 : (3-bromo-4-methyl-phenoxy)-tert-butyl-dimethyl-silane tert-Butyldimethylsilyl chloride (0.18 g) is added to a solution of 3-bromo-4-methyl- phenol (0.20 g) and triethylamine (0.23 ml_) in dichloromethane (3 ml_) chilled in an ice bath. 4-Dimethylaminopyridine (13 mg) is added and the solution is stirred at room temperature overnight. Dichloromethane is added and the solution is washed with 1 M hydrochloric acid, aqueous NaHC03 solution, and brine, and dried (MgS04). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. Yield: 0.25 g (78% of theory); LC (method 1 ): tR = 1 .59 min.
78%
With dmap; triethylamine; In dichloromethane; at 20℃;Cooling with ice;
Intermediate 71{(S)-6-[(R)-4-(5-Hydroxy-2-methyl-phenyl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester Step 1: (3-bromo-4-methyl-phenoxy)-tert-butyl-dimethyl-silanetert-Butyldimethylsilyl chloride (0.18 g) is added to a solution of <strong>[60710-39-6]3-bromo-4-methyl-phenol</strong> (0.20 g) and triethylamine (0.23 mL) in dichloromethane (3 mL) chilled in an ice bath. 4-Dimethylaminopyridine (13 mg) is added and the solution is stirred at room temperature overnight. Dichloromethane is added and the solution is washed with 1 M hydrochloric acid, aqueous NaHCO3 solution, and brine, and dried (MgSO4).The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. Yield: 0.25 g (78% of theory); LC (method 1): tR=1.59 min.
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