Methyl iodide → N-(3-(1-methyl-1H-indol-2-yl)propyl)-2-(S)-(2,2,2-trifluoro-acetylamino)butanamide

Participants

Reaction Steps

A 20 mL cintillation vial was charged with (S)—N-(3-(1H-indol-2-yl)propyl)-2-(2,2,2-trifluoroacetamido)butanamide (60 mg, 0.169 mmol) and dimethylformamide (0.75 mL). Sodium hydride (6.0 mg, 0.25 mmol) was added and the resulting mixture was stirred at room temperature for 15 minutes. Methyl iodide (0.012 mL, 0.193 mmol) was added and the resulting mixture was stirred at room temperature for 1 h. The resulting mixture was then concentrated in-vacuo and purified via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-50:50 Heptane:EtOAc) to yield N-[3-(1-methyl-1H-indol-2-yl)-propyl]-2-(S)-(2,2,2-trifluoro-acetylamino)-butyramide. 1H NMR (300 MHz, CDCl3) δ7.52 (d, J=7.7 Hz, 1H), 7.25-7.28 (m, 1H), 7.14-7.19 (m, 1H), 7.04-7.10 (m, 1H), 6.26 (s, 1H), 4.31-4.36 (m, 1H), 3.64 (s, 3H), 3.33-3.46 (m, 2H), 2.75-2.82 (m, 2H), 1.80-2.09 (m, 3H), 1.59-1.71 (m, 1H), and 0.87-0.92 (m, 3H); MS (ES+) 370 (M+1).

Provenance & Evidence