Sodium Carbonate → (2S,4R)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-p-tolyl-pyridin-3-yl]-N-methyl-isobutyramide

Participants

Reaction Conditions

Reaction Steps

A mixture of 150 mg (0.238 mmol) (2S,4R)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-iodo-pyridin-3-yl]-N-methyl-isobutyramide, 38.7 mg (0.284 mmol) 4-tolylboronic acid, 0.75 ml 2 N sodium carbonate solution, 5.3 mg (0.024 mmol) palladium acetate and 12 mg (0.048 mmol) triphenylphosphine in 1.5 ml 1,2-dimethoxyethane was stirred at 80° C. for 2 h. The reaction mixture was treated with 10 ml 2 N sodium carbonate solution and extracted with two 15-ml portions of ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated. Flash chromatography gave 112 mg (79%) of the title compound as a yellow foam. MS m/e (%): 596 (M+H+, 100)

Provenance & Evidence