Cesium fluoride → (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2',4'-difluoro-6'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate (0.25 g, 0.428 mmol, 1 equiv) and (S)-tributyl(2,4-difluoro-6-(pent-4-en-2-yloxy)phenyl)stannane (0.25 g, 0.513 mmol, 1.2 equiv) in DMF (2 mL, sparged with nitrogen for 10 min) was added Pd(PPh3)4 (49 mg, 0.043 mmol, 0.1 equiv), CsF (195 mg, 1.28 mmol, 3 equiv), and CuI (20 mg, 0.107 mmol, 0.25 equiv). The reaction was heated at 80° C. for 2 h. After 2 h, more stannane (300 mg) was added. Stir for 2 h and remove from heat. Upon cooling to ambient temperature, the reaction was diluted with EtOAc, washed with water, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (160 mg, 53%) as a film. LCMS (ESI, M+1): 702.25.

Provenance & Evidence