Potassium Carbonate → HCID 59619234, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled through a mixture of (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-(tetrahydro-pyran-4-yloxy)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (40 mg, 0.0707 mmol, example 169) and K2CO3 (20 mg, 0.1415 mmol) in n-butanol (2 ml) for 10 minutes. Then triphenyl-phosphine (1.48 mg, 0.00566 mmol) and palladium acetate (0.318 mg, 0.001415 mmol) were added and the reaction mixture was stirred at 100° C. for 2 h. The mixture was allowed to cool to room temperature, the solvent was removed and the remaining residue was diluted with water and extracted 3 times with EtOAc. The combined extracts were washed with brine, dried (Na2SO4) and evaporated. The remaining residue was purified by silica column chromatography (DCM/MeOH 98:2) to obtain the title compound contaminated with a small amount of triphenyl-phosphine oxide. This material was triturated with a small amount of ether to give the title compound (25 mg, 73%) as white solid. MS (EI): 487.3 (M+H)+.

Provenance & Evidence