3,4-Dimethylaniline → 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide

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Reaction Steps

A mixture of 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (150 mg, 490 μmol), 3,4-dimethylaniline (60 mg, 500 μmol), HATU (280 mg, 740 μmol), and triethylamine (137 μL, 99 mg, 980 μmol) in DMF (10 mL) was stirred 18 h at ambient temperature. The solution was decanted into ethyl acetate and extracted once with water and five times with brine, then dried, filtered, and the solvent removed under reduced pressure to leave an oil, which was purified by chromatography using a gradient of 10-50% heptane/ethyl acetate to give 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide. 1H NMR (CDCl3, 400 MHz) δ 8.53 (s, broad, 1H), 8.11 (s, 1H), 7.83 (s, 1H), 7.75 (d, J=8.2 Hz, 1H), 7.58 (d, J=8.3 Hz, 1H), 7.46 (m, 3H), 7.38 (dd, J=10.4, 2.1 Hz, 1H), 7.31 (m, 1H), 7.13 (d, J=8.2 Hz, 1H), 6.72 (s, 1H), 2.29 (s, 3H), 2.25 (s, 2H). MS (m/z) 409.1 (M+1); retention time=1.68 min (Method 10). High Resolution, MS (M+H): theory, 409.0874; measured 409.0867.

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