Tin tetrachloride → HCID 178496867, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-(methoxy carbonyl)cyclopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-(methoxy carbonyl)cyclopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 142-B) (680 mg, 1.078 mmol) in dichloromethane (10.0 mL) at 0° C. was added a 1.0M solution of SnCl4 in dichloromethane (10.78 mL, 10.78 mmol). This mixture was stirred for 30 min at 0° C. followed by 60 min at room temperature. The reaction was partitioned between EtOAc and a saturated aqueous sodium bicarbonate solution. The layers were filtered through Celite® to remove emulsion formed and then the layers were separated. The organic phase was brine washed, dried over Na2SO4 and concentrated in vacuo to afford the crude product. This material was purified using FCC eluting with ethyl acetate/heptane (30-100%) to afford the title compound. MS (ESI+) m/z 401.1 (M+H).

Provenance & Evidence