Diisopropylethylamine → (S)-3-[4-(1H-indazol-5-ylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

5-Bromo-1H-indazole (200.9 mg, 1.02 mmol), Pd2(dba)3 (115.9 mg), Xantphos (145.9 mg) and DIPEA (0.188 mL) were added to a solution of (S)-3-(4-mercapto-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (285 mg, 1.02 mmol) in 1,4-dioxane (4 mL) under argon atmosphere. The reaction mixture was heated at 100° C. for 18 hours, then cooled to 5° C. and a solution of 10% KHSO4/Na2SO4 was added. The mixture was filtered, the filter cake was washed with EtOAc, and the filtrate was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3) to give 252 mg (62% yield) of (S)-3-[4-(1H-indazol-5-ylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence