Ammonium Chloride → 1-(3-cyano-benzoyl)-3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

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Reaction Steps

KHMDS (0.5 M in toluene, 1.46 mL, 0.73 mmol) is added to a solution of 3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile (Example 6, 122 mg, 0.480 mmol) in THF (10 mL) at room temperature. After 5 min, 3-cyanobenzoyl chloride (178 mg, 1.08 mmol) is added. The mixture is stirred under N2 for 1 h, whereupon aqueous ammonium chloride (0.5 mL) is added. The solvents are removed in vacuo and the residue is purified by Xbridge RP18 with a 0.1% aqueous ammonium hydroxide in acetonitrile gradient to give 1-(3-cyano-benzoyl)-3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile. 1H NMR (400 MHz, CDCl3) δ ppm 2.35 (s, 3H), 7.37-7.44 (m, 1H), 7.47-7.52 (m, 1H), 7.60-7.64 (m, 1H), 7.68-7.83 (m, 5H), 8.01 (d, J=1.5 Hz, 1H), 8.51 (d, J=4.5 Hz, 1H), 8.53 (s, 1H). HRMS (ESI) m/z 363.1247 [(M+H)+ Calcd for C23H15N4O: 363.1246].

Provenance & Evidence