Tin tetrachloride → HCID 178489077, 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)-2,2,2-trifluoro-1-((5-methyl-1,3,4-oxadiazol-2-yl)methoxy)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate compound and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-((5-methyl-1,3,4-oxadiazol-2-yl)methoxy)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 35-K) (38 mg, 0.051 mmol) in dichloromethane (1.0 mL) at 0° C. was added a 1.0M solution of SnCl4 in dichloromethane (0.51 mL, 0.51 mmol). This mixture was stirred at 0° C. for 30 min and then warmed to room temperature and stirred for an additional 1.0 hr. The crude reaction mixture was diluted with ethyl acetate and a saturated sodium bicarbonate solution and the layers were passed over Celite® and then separated. The organic phase was washed with brine solution, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified using FCC eluting with ethyl acetate/heptane (0-100%) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.00 (br.s., 1H) 11.10 (br. s., 1H) 8.30 (s, 1H) 7.82-7.93 (m, 1H) 7.49-7.64 (m, 1H) 7.36 (t, J=2.91 Hz, 1H) 6.76 (s, 1H) 6.68 (br. s., 1H) 4.47-4.82 (m, 2H) 3.11 (s, 3H) 2.40 (s, 3H) 1.24 (s, 3H). HRMS calcd. for C24H19F3N6O3 (M+H)+ 497.1535. found 497.1504.

Provenance & Evidence