Tert-Butanesulfinamide → (+/-)-tert-Butyl 4-((tert-butylsulfinylimino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 126-A) (711 mg, 1.648 mmol) and 2-methyl-2-propanesulfinamide (599 mg, 4.94 mmol) in toluene (16.5 mL), Zr(O-t-Bu)4 (4.33 mL, 8.24 mmol) was added at room temperature. After 2 hours the reaction mixture was diluted with EtOAc and brine. The resulting mixture was filtered through Celite® and the organic layer of the filtrate was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc:Heptanes) to provide the title compound. MS (ESI+) m/z 535.2 (M+H).

Provenance & Evidence