Triethylamine → HCID 58026125, compound

Participants

Reaction Steps

To a solution of (S)-6-(4-chloro-2-methanesulfonylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (15.6 g, 40.8 mmol), triethylamine (23.0 mL, 165 mmol), and (4-iodo-6-methanesulfonylpyridin-3-yl)carbamic acid tert-butyl ester (18.0 g, 45.2 mmol) in 150 mL of DMF was added CuI (1.6 g, 8.4 mmol) and Pd(PPh3)2Cl2 (3.0 g, 4.3 mmol) as one mixed solid batch. The mixture was stirred at room temperature for 18 hours resulting in the color changing to deep red. Saturated aqueous ammonium chloride solution and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, brine, dried over sodium sulfate, filtered through CELITE® filter aid, and evaporated. The crude material was separated by flash column chromatography using a 0-75% EtOAc/hexanes gradient. Evaporation of the solvent yielded an off-white foam as the pure {4-[(S)-6-(4-chloro-2-methanesulfonylphenyl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-6-methanesulfonylpyridin-3-yl}carbamic acid tert-butyl ester (18.1 g, 68%).

Provenance & Evidence