Nitrogen → HCID 66990918, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of cis-1-[6-chloro-2-(methylamino)-4-pyrimidinyl]-N-(phenylmethyl)-6-(trifluoromethyl)-3-piperidinecarboxamide (100 mg, 0.234 mmol) and (4-cyano-3-fluorophenyl)boronic acid (57.8 mg, 0.351 mmol) in 1,4-dioxane (2 mL) was added saturated aqueous NaHCO3, and N2 gas was bubbled through the mixture for 10 minutes into a 5 mL microwave vial. Pd(Ph3P)4 (40.5 mg, 0.035 mmol) was added, and N2 gas was bubbled through the mixture for an additional 5 minutes. The vial was capped, and the reaction mixture was heated overnight over a hot plate at 100° C. The reaction was diluted with water (5 mL), and the resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting yellow oil was purified on Biotage SNAP 10 g column with gradient of 0 to 40% EtOAc in Hexane over 30 minutes to afford the title compound (66 mg) as a yellow oil. LC-MS (ES) m/z=513 [M+H]+.

Provenance & Evidence