Dabco → HCID 178427328, compound

Participants

Reaction Steps

A solution of 7-chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole (67 mg, 0.133 mmol), 3,4-diaminobenzonitrile (26.6 mg, 0.200 mmol) and DABCO (44.8 mg, 0.399 mmol) in NMP (0.5 mL) was stirred at 110° C. After stirring overnight, the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-100% EtOAc in heptanes) to provide 2-((7-chloro-5-methyl-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile. The obtained compound was dissolved in EtOH (5.0 mL), and KOH (0.118 g, 2.105 mmol) and isoamylamine (0.489 mL, 4.21 mmol) were added, and the mixture was stirred at 100° C. in the microwave for 30 minutes. The reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.50 (s, 1H) 11.33 (br. s., 1H) 7.93 (s, 1H) 7.57 (d, J=8.84 Hz, 1H) 7.47 (dd, J=8.34, 1.52 Hz, 1H) 7.33 (t, J=2.78 Hz, 1H) 7.06 (s, 1H) 6.52-6.63 (m, 1H) 4.45 (s, 2H) 2.39 (s, 3H). HRMS calcd. for C18H13ClN4 (M+H)+ 321.0902. found 321.0906.

Provenance & Evidence