N-methyl-2-pyrrolidone → HCID 58403540, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 230 (454 mg, 2.16 mmol) in NMP (4.5 mL) under argon atmosphere was added Zn(CN)2 (252 mg, 2.16 mmol), zinc powder (27 mg, 0.43 mmol), Pd2(dba)3 (0) (293 mg, 0.32 mmol), and dppf (358 mg, 0.65 mmol). The solution was heated at 140° C. for 18 h, the mixture was cooled and partitioned between EtOAc (100 mL) and H2O (30 mL). The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to dryness in vacuo. The residue was purified by SiO2 chromatography eluting with 10% EtOAc/petroleum ether to afford 200 mg (59%) of 3-methyl-1H-indole-4-carbonitrile (232) as white solid: MS (ESI) m/z=157.1 [M+1]+.

Provenance & Evidence