Triethylamine → HCID 58092314, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(6-bromo-1-methyl-1H-indol-3-yl)ethanamine (6.50 g, 25.7 mmol) in CH2Cl2 (50 mL) were added 4-bromobutyryl chloride (4.50 mL, 38.6 mmol) and NEt3 (7.20 mL, 51.4 mmol). After 2 h, the reaction mixture was diluted with CH2Cl2 and filtered through a layer of Celite. The filtrate was concentrated to give a brown oil. The oil was diluted with benzene (120 mL) and treated with POCl3 (12 mL, 0.13 mol). The reaction mixture was heated at reflux for 1 h. After the mixture was concentrated, the residue was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2) to give the crude product (6.1 g) as a brown oil. The oil was diluted with EtOH and cooled to 0° C. NaBH4 (0.60 g, 16 mmol) was added, and the reaction was stirred from 0° C. to room temperature for 1 h. After the solution was concentrated, the residue was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2) to give the title compound (1.66 g, 34% in three steps) as a yellow foam: 1H NMR (300 MHz, CDCl3) δ 7.45 (d, J=1.5 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.23 (dd, J=8.4, 1.5 Hz, 1H), 4.79 (t, J=6.6 Hz, 1H), 3.63 (s, 3H), 3.44-3.25 (m, 3H), 3.16-3.10 (m, 1H), 2.99-2.96 (m, 2H), 2.70-2.61 (m, 1H), 2.26-1.96 (m, 3H); ESI MS m/z 305 [M+H]+.

Provenance & Evidence