Isoamylamine → HCID 178424944, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-2-(1-hydroxy-1-(5-isopropyl-7-methyl-1-tosyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(1-hydroxy-1-(7-methyl-5-propyl-1-tosyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (110 mg, 0.215 mmol), isoamylamine (94 mg, 1.073 mmol), and KOH (60.2 mg, 1.073 mmol) was stirred at 100° C. for 0.75 h under the microwave irradiation. The reaction mixture was diluted with CH2Cl2. The mixture was filtered through SiO2. The SiO2 cake was washed with a mixture of CH2Cl2/MeOH (c.a. 6/1). Combined organic solution was concentrated and purified by silica gel flash column chromatography (CH2Cl2/EtOAc=82/18, isocratic) to give (±)-2-(1-hydroxy-1-(5-isopropyl-7-methyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile as a pure isomeric form. 1H NMR (400 MHz, ACETONITRILE-d3 with about 5 μL TFA) δ ppm 9.28 (br. s., 1H), 8.05 (s, 1H), 7.73 (d, J=8.60 Hz, 1H), 7.69 (dd, J=1.30, 8.60 Hz, 1H), 7.19 (dd, J=2.80, 2.90 Hz, 1H), 7.00 (s, 1H), 6.66 (dd, J=2.30, 3.00 Hz, 1H), 2.90-3.06 (m, 1H), 2.47 (s, 3H), 2.28 (s, 3H), 0.95 (d, J=6.82 Hz, 3H), 0.92 (d, J=6.57 Hz, 3H). HRMS calcd. for C22H22N4O (M+H)+ 359.1867. found 359.1865.

Provenance & Evidence