Sodium Carbonate → ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-{2-fluoro-4-[[(2-nitrophenyl)sulfonyl](4-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1H-inden-1-yl)amino]phenyl}propanoate (3.14 g, 4.76 mmol), (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (2.0 g, 7.14 mmol) and sodium carbonate (1.51 g, 14.3 mmol) were dissolved in a mixture of water (10 mL), ethanol (10 mL) and toluene (30 mL), and the air was substituted with argon gas. Tetrakis(triphenylphosphine)palladium(0) (0.275 g, 0.24 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 120° C. for 16 hr. After cooling, the reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3%-60% ethyl acetate/hexane) to give ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate as a yellow oil. The obtained oil was dissolved in tetrahydrofuran (30 mL), tetrabutylammonium fluoride (1 M THF solution, 2.43 mL, 2.43 mmol) was added under stirring at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-60% ethyl acetate/hexane) to give the title compound (1.46 g, yield 78%, 2 steps) as a yellow oil.

Provenance & Evidence