Nitrogen → HCID 66991246, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of cis-1-[6-chloro-2-(methylamino)-4-pyrimidinyl]-N-cyclopentyl-6-(trifluoromethyl)-3-piperidinecarboxamide (46 mg, 0.113 mmol) and (4-cyano-3-fluorophenyl)boronic acid (28.0 mg, 0.170 mmol) in 1,4-dioxane (1 mL) was added saturated aqueous NaHCO3 (0.5 mL), and N2 gas was bubbled through the resulting mixture for 10 minutes into a 5 mL sealable vial. Pd(Ph3P)4 (19.7 mg, 0.017 mmol) was added, and N2 was bubbled for an additional 5 minute. The vial was capped, and the reaction mixture was heated at 100° C. overnight. The reaction was diluted with water (5 mL) and then extracted with EtOAc (3×10 mL). The organics were dried over MgSO4, filtered and concentrated. The resulting yellow oil was then purified on Biotage SNAP column 10 g with gradient of 0 to 40% EtOAc in Hexane to afford the title compound (37 mg) as a yellow oil. LC-MS (ES) m/z=491 [M+H]+.

Provenance & Evidence