Diisobutylaluminumhydride → HCID 86709317, compound

Participants

Reaction Steps

A solution of tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-5H-chromeno[2,3-c]pyridin-5-yl)acetate (isomer A) (720 mg, 1.359 mmol) in dry THF (5.5 mL) was brought to −78° C. and diisobutylaluminum hydride (5.44 mL, 5.44 mmol) was added slowly. The mixture was brought to 0° C. after diisobutylaluminum hydride addition, and stirred at this temperature for 0.5 hr. The reaction mixture was quenched with saturated Rochelle's salt (˜40 mL) and stirred at RT for overnight. The organic layer was separated and the aqueous phase was extracted by EtOAc. The combined organics were washed with saturated NaCl aqueous solution, dried over MgSO4, filtered, and concentrated to afford N-(7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide as off-white solid that was advanced without further purification.

Provenance & Evidence