(E)-tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate → tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Steps

A solution of compound 19b (130 mg, 0.210 mmol) in MeOH (50 mL) was evacuated and back flushed with Argon gas three times before Pd/C (10%, 100 mg) was added. The mixture was evacuated and back flushed with H2, and was stirred at rt under H2 (in a balloon) for 3 h. The reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated under reduced pressure to leave a brown oil, which was purified by flash column chromatography on silica gel, eluting with EtOAc/heptane (0-100%). Compound 20a was obtained as an off-white solid (69.0 mg, 53% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H40N8O3: 621.3 (M+H). found: 621.4.

Provenance & Evidence