Sodium Bicarbonate → ((3S)-3-Hydroxypyrrolidin-1-yl) (8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

Participants

Reaction Steps

8-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (1.77 g) was dissolved in DMF (22 mL), and HATU (2.72 g), (S)-pyrrolidin-3-ol (529 μL) and triethylamine (1.08 mL) were added thereto. The reaction mixture was stirred at room temperature for 1 hr, saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a solid (1.38 g). The solid (100 mg) was recrystallized from ethyl acetate/hexane to give the title compound (89 mg).

Provenance & Evidence