Sodium hydride → HCID 89462964, compound

Participants

Reaction Conditions

Reaction Steps

An ice cold solution of methyl 2-(1-benzyl-3-cyano-N-methyl-1H-pyrrole-2-carboxamido)acetate (9.2 g, 29.6 mmol) in Tetrahydrofuran (THF) (100 mL) was treated with NaH, 60% dispersion in mineral oil, (1.536 g, 38.4 mmol) and the mixture was stirred at 0° C. for 30 minutes, then allowed to warm to room temperature and stirred an additional 2 hours at ambient temperature. The mixture was quenched with saturated NH4Cl solution at 0° C. and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford methyl 1-benzyl-4-imino-6-methyl-7-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (9.0 g, 28.9 mmol, 98% yield) as a pale yellow solid which was used in the next step without any further purification. 1H NMR (400 MHz, DMSO-d6) ppm 7.42-7.51 (m, 1H) 7.18-7.36 (m, 5H) 6.78-6.89 (m, 1H) 6.39-6.54 (m, 2H) 5.77 (s, 2H) 3.78 (s, 3H) 3.38 (s, 3H); LCMS (m/z) ES+=312 (M+1).

Provenance & Evidence