Chlorotrimethylsilane → (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

Participants

Reaction Steps

To a solution of compound 19a (50.0 mg, 0.101 mmol) in DMF (3 mL) was added 2-methylquinoline (13.2 μL, 0.101 mmol) and chlorotrimethylsilane (38.6 μL, 0.304 mmol). The reaction mixture was stirred in a 10 mL sealed tube for 2 h at 80° C. After cooling to rt, the reaction mixture was poured into water (20 mL). The mixture was adjusted to basic using saturated NaHCO3 solution, and was extracted with DCM (2×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Compound 19b was obtained as a yellow solid (40.0 mg, 64% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H38N8O3: 619.3 (M+H). found: 619.3.

Provenance & Evidence