1,2-Dichloroethane → N-Methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-2-phenoxybenzamide

참여 물질

반응 단계

EDC (230 mg, 1.2 mmole) was added to a solution of 2-phenoxybenzoic acid (214.2 mg, 1.0 mmole), 1-methyl-2-(methylaminomethyl)indole (209.1 mg, 1.2 mmole), HOBt.H2O (162.2 mg, 1.2 mmole), and triethylamine (0.35 mL, 2.5 mmole) in DMF (5 mL) at RT. After 16.5 hr, the reaction was concentrated, and the residue was reconcentrated from xylenes/CHCl3 to remove residual DMF. Flash chromatography on silica gel (40% EtOAc/hexanes) gave the title compound (393.5 mg, quantitative) as a nearly colorless, very viscous oil: 1H NMR (360 MHz, CDCl3) indicated an approximately 5:1 mixture of amide rotamers; for the major rotamer: δ 7.56 (d, J=7.9 Hz, 1H), 6.98-7.50 (m, 9H), 6.95 (d, J=7.6 Hz, 2H), 6.87 (d, J=7.5 Hz, 1H), 6.49 (s, 1H), 4.40-5.40 (m, 2H), 3.62 (s, 3H), 2.84 (s, 3H); for the minor rotamer: δ 6.80-7.50 (m, 13H), 6.47 (s, 1H), 4.40-5.40 (m, 2H), 3.56 (s, 3H), 2.98 (s, 3H); MS (ES) m/e 371 (M+H)+.

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