Acetonitrile → HCID 178435789, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-2-((5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)(methoxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile, (±)-2-((5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)(methoxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (mixture, 650 mg, 1.03 mmol) and LiBF4 in CH3CN (1M, 10 mL, 10 mmol)/H2O (1 mL) was stirred at 75° C. for 14 h. The mixture was cooled to room temperature and poured into 5% NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic phase was successively washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel flash column chromatography (heptanes/EtOAc=55/45) to give the title compound. MS (ESI+) m/z 499.2 (M+H).

Provenance & Evidence