Dimethylacetamide → 2,3-dihydro-1H-indole-4-carbonitrile

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Reaction Steps

Degas a solution of 4-bromo-2,3-dihydro-1H-indole (250 mg, 1.224 mmol) in dimethylacetamide (2 mL) under Ar. To this add zinc cyanide (147 mg, 1.224 mmol) followed by tetrakis-(triphenylphosphine) palladium(0) (143 mg, 0.123 mmol) and heat the reaction under argon in a sealed tube at 100° C. for 4 h. Quench the cooled reaction with sat. NH4Cl (50 mL) and extract with EtOAc (3×50 mL). Wash the organics with water (50 mL), dry (Na2SO4), then concentrate in vacuo to give a gum. Purify by silica gel chromatography eluting with 5% to 30% EtOAc/hexane. Pool and concentrate fractions containing product then dissolve the residue in Et2O (5 mL) and hexane (50 mL). Reconcentrate this to a solid. Suspend in hexane and filter washing with hexane to afford the product 2,3-dihydro-1H-indole-4-carbonitrile as a powder (131 mg, 0.863 mmol). MS, electrospray 145.2 (M+H), rt 1.02 min.

Provenance & Evidence