Chloride → 1-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide

Participants

Reaction Steps

Triethylamine (3.2 mL, 22.8 mmol) in 30 mL of methylene chloride was added dropwise over 2 h to a mixture of 2-(6-methoxy-naphthalen-2-yl)-2-oxo-ethyl-ammonium; chloride (2.47 g, 11.4 mmol), prepared in step 3 of Example 1, and 1-methyl-1H-indole-3-carbonyl chloride (2.21 g, 11.4 mmol), prepared in the previous step, in 100 mL of methylene chloride at room temperature. After the addition of the reaction was stirred at room temperature for 16 h (overnight). The reaction was diluted with methylene chloride, extracted twice with 1N HCl, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide (3.86 g, 91%) as a yellow solid, mp 177-180° C. Elemental Analysis for C23H20N2O3 Calc'd: C, 74.18; H, 5.41; N, 7.52. Found: C, 72.68; H, 5.34; N, 7.29

Provenance & Evidence