Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate → Methyl 1-butyl-4-cyano-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 1-butyl-4-iodo-1H-indole-6-carboxylate (Example SP-218, Step 4) (1.47 g) in N-methyl pyrrolidinone (15 mL) was added copper (I) cyanide (1.1 g). The mixture was heated to 150° C. for 6 h, removed from heat and cooled to room temperature. The mixture was partitioned between water and ethyl acetate and the layers were separated. The organic layer was washed three times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 20% ethyl acetate as eluent to give 0.5 g of the title compound: 1H NMR (CDCl3) δ 0.955, 1.32, 1.85, 3.98, 4.23, 6.76, 7.43, 8.16, 8.30.

Provenance & Evidence