2,6-Di-tert-butyl-4-methylphenol → (1S,2S)-2-(4-{(R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5-trifluoromethyl-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

(1S,2S)-2-[4-((R)-4-Bromo-5-trifluoromethyl-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (200 mg, 0.43 mmol), 4-(tertbutyldimethylsilyloxy)phenylboronic acid (118 mg, 0.47 mmol) potassium carbonate (176 mg, 1.28 mmol), 2,6-di-tert-butyl-4-methylphenol (47 mg, 0.21 mmol), tricyclohexylphosphine (10 mg, 0.03 mmol), and Pd2(dba)3 (16 mg, 0.02 mmol) are suspended in a mixture of dioxane (1.7 mL) and water (0.6 mL) in a sealed tube and heated at 110° C. for 4 hours. The mixture is diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried and concentrated under vacuum. The residue is purified by flash chromatography (eluent: 0-30% EtOAc in cyclohexane) to give the title compound (Yield 90 mg)

Provenance & Evidence