Dimethylformamide → 4-[1-(Cyano-methyl-methyl)-6-nitro-1H-indol-3-yl]-2-fluoro-benzonitrile

Participants

Reaction Steps

Method LL Add 2-Fluoro-4-(6-nitro-1H-indol-3-yl)-benzonitrile (1.24 mmoles; 350 mg), cesium carbonate (3.61 mmoles; 1.18 g) and dimethylformamide (10 mL) to a reaction vessel equipped with a stir bar. Stir this mixture for 10 minutes at room temperature then add toluene-4-sulfonic acid cyano-methyl-methyl ester (3.11 mmoles; 701 mg). Stir the resulting mixture for 5 hours at 55° C. Dilute this material with water (25 mL), brine (50 mL) and ethyl acetate (50 mL). Separate the organics and extract the resulting aqueous mixture with ethyl acetate (2×) and dichloromethane containing 10% methanol (2×). Combine the organics and concentrate in vacuo to about ½ volume. Wash the resulting mixture with water and evaporate the solvent in vacuo. Triturate the resulting yellow solids with hot dichloromethane. Collect the solids by vacuum filtration and rinse them with 50% dichloromethane/hexane to give the title compound (196 mg, 47%) yellow amorphous solid. MS (IS−) m/e 333.0 (M−1), 393.0 (M−1+OAc).

Provenance & Evidence