Sodium hydride → HCID 136342114, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-cyanooxindole (360 mg, 2.27 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (106 mg, 4.41 mmol). The greenish reaction mixture was stirred for 50 min whereafter 6-chloronicotinic acid ethyl ester (350 mg, 1.89 mmol) dissolved in N,N-dimethylformamide (5 mL) was added. The reaction mixture was heated at 110° C. for 30 min and water (50 mL) and saturated NH4Cl(aq) (20 mL) was added, followed by extraction with ethyl acetate. The phases were separated and the organic phase contained the title compound as a precipitation that was filtered off. The solvent was concentrated in vacuo and additional product precipitated that was filtered to give 200 mg (34% yield) of the title compound in total: 1H NMR (DMSO-d6, 300 MHz) δ 14.50 (br s, 1 H), 11.00 (s, 1 H), 8.73 (s, 1 H), 7.95 (s, 2 H), 7.80 (s, 1 H), 7.48 (s, 1 H), 6.95 (d, J=7 Hz, 1 H), 4.50-4.15 (m, 2 H), 1.32 (t, J=7 Hz, 3 H).

Provenance & Evidence