Sodium cyanoborohydride → HCID 178488390, compound

Participants

Reaction Steps

(±)-2-(1-Methoxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (Example 27-B) (0.213 g, 0.591 mmol) was dissolved in acetic acid (1.970 mL), and sodium cyanoborohydride (0.12 g, 1.910 mmol) was added at room temperature. The reaction was stirred at the same temperature for 1 hour. The reaction was placed in an ice bath and quenched with 1N aq. NaOH (20 mL) until pH>7. EtOAc was added and the organic layer was removed, dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes) to give the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.11 (s) 7.84 (m) 7.65 (s) 7.43-7.54 (m, 1H) 7.34-7.42 (m) 6.43 (s, 1H) 3.50-3.59 (m, 2H) 3.27-3.36 (m, 2H) 3.24 (s, 3H) 3.12 (s, 3H) 2.13 (s, 3H) 2.05 (s, 3H). HRMS calcd. for C21H22N4O2 (M+H)+, 303.1604. found 303.1615

Provenance & Evidence