Trifluoroacetic acid → HCID 178423615, compound

Participants

Reaction Steps

2-((5,7-Dimethyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (35 mg, 0.117 mmol) was suspended in DCM (1 mL), triethylsilane (0.37 mL, 2.33 mmol) and then TFA (0.5 mL) were added and the reaction was stirred at room temperature. After 1 hour the reaction was concentrated and then the resulting residue was dissolved in EtOAc and treated with 1 mL of aq. ammonium hydroxide. The residue was purified via FCC (0-100% EtOAc in heptanes) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.47 (d, J=15.66 Hz, 1H) 8.02 (m) 7.88 (m) 7.56 (m) 7.50-7.54 (m) 6.60 (s, 1H) 5.08 (br. s., 1H) 4.08 (d, J=3.54 Hz, 2H) 3.40 (t, J=8.46 Hz, 2H) 2.91 (t, J=8.46 Hz, 2H) 2.09 (s, 3H) 1.94-2.03 (m, 3H). HRMS calcd. for C19H18N4 (M+H)+, 303.1604. found 303.1615.

Provenance & Evidence