Sodium hydride → methyl 9-(4-fluorobenzyl)-4-hydroxy-2-methyl-1-oxo-2,9-dihydro-1H-pyrido[3,4-b]indole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

An ice cold solution of methyl 1-(4-fluorobenzyl)-2-((2-methoxy-2-oxoethyl)(methyl)carbamoyl)-1H-indole-3-carboxylate (3 g, 7.27 mmol) in N,N-Dimethylformamide (DMF) (36.4 ml) was treated with NaH (0.378 g, 9.46 mmol). After 1 h, the reaction mixture was cooled to 0° C. and slowly quenched with H2O. The mixture was extracted with EtOAc and the organic layer washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by ISCO (0-3% DCM/MeOH) to afford methyl 9-(4-fluorobenzyl)-4-hydroxy-2-methyl-1-oxo-2,9-dihydro-1H-pyrido[3,4-b]indole-3-carboxylate (1.1 g, 2.89 mmol, 39.8% yield) as an orange solid. LCMS (m/z) ES+=381 (M+1).

Provenance & Evidence