Sodium t-butoxide → HCID 78322868, compound

Participants

Reaction Conditions

Reaction Steps

5-(2-Chloro-primidin-4-yl)-2-((S)-3-fluoro-pyrrolidin-1-yl)-nicotinonitrile (8) (100 mg, 0.329 mmol), 3-amino-N-(1-methyl-piperidin-4-yl)-benzamide (115 mg, 0.493 mmol), Pd2(dba)3 (30 mg, 0.0327 mmol), NaOtBu (48 mg, 0.499 mmol) and Dave-Phos (130 mg, 0.330 mmol) were dissolved in 1,4-dioxane (3 mL). Nitrogen was bubbled through the stirred mixture for 5 minutes. The reaction mixture was then stirred at 120° C. in the microwave (250 W, stirring) for 2 hours. The solvent was evaporated in vacuo and the residue dissolved in DMSO (3 mL). The crude product was purified by reversed phase preparative LC-MS. Fractions containing desired product were combined and the MeOH evaporated in vacuo. The aqueous solution was frozen (−78° C.) and the solvent evaporated in vacuo (freeze dried). The title compound was obtained as an off-white solid (68 mg, 38%); LCMS, Rt=4.94 min (Method A), m/z 501 (MH+).

Provenance & Evidence