Triethylamine → HCID 86632970, compound

Participants

Reaction Steps

To a solution of N-methyl-3-(5-nitro-1H-indol-3-yl)cyclohexanamine (0.40 g, 1.46 mmol) in 1,4-dioxane (10 mL) was added (Boc)2O (0.35 g, 1.61 mmol) and triethyl amine (0.40 mL, 2.92 mmol) and the resulting mixture left to stir overnight at room temperature. The solvent was evaporated and the crude purified on column chromatography (EtOAc:Hexanes, 1:1) to give the title compound as a yellow solid (0.40 g, 73%). 1H-NMR (CDCl3) δ 1.34-1.44 (m, 1H), 1.49 (s, 9H), 1.57-1.69 (m, 3H), 1.78-1.86 (m, 1H), 1.92-2.00 (m, 1H), 2.03-2.10 (m, 2H), 2.78 (s, 3H), 2.95-3.06 (m, 1H), 3.96-4.27 (m, 1H), 7.11 (d, 1H, J=1.8 Hz), 7.38 (d, 1H, J=9.0 Hz), 8.10 (dd, 1H, J=2.1, 9.0 Hz), 8.37 (s, 1H, NH), 8.61 (d, 1H, J=2.1 Hz); EI-MS (m/z, %), 242 (100), 373 (20).

Provenance & Evidence