Sodium Bicarbonate → (3S,6R)-1-[6-(4-Cyano-3,5-difluorophenyl)-2-(methylamino)-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide

Participants

Reaction Conditions

Reaction Steps

(3S,6R)-1-[6-chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide (100 mg, 0.267 mmol) and (4-cyano-3,5-difluorophenyl)boronic acid (73.4 mg, 0.401 mmol) were dissolved in 1,4-Dioxane (2 mL) in a 5 mL sealable vial then added saturated NaHCO3 (1 mL). Nitrogen gas was bubbled through the mixture for 10 min. Then Pd(Ph3P)4 (37.1 mg, 0.032 mmol) was added and nitrogen gas bubbled for an additional 5 min. The vial was capped the reaction was heat at 100° C. overnight. The reaction was diluted with water (5 mL) and then extracted with EtOAc (3×10 mL). Organic were combined, dried over MgSO4, filtered and concentrated. The yellow oil was then purified on a 10 g Biotage SNAP column with gradient of 0 to 40% EtOAc in Hexane. LC-MS (ES) m/z=477 [M+H]+.

Provenance & Evidence