Hydrochloric Acid → HCID 86689261, compound

Participants

Reaction Steps

Butyllithium solution, 2.5m in hexanes (1.257 mL, 3.14 mmol) was added dropwise to a solution of 1-bromo-2-(ethoxymethoxy)benzene (0.726 g, 3.14 mmol) in THF 20 mL at −78° C. The reaction was stirred for 25 min. Then N-(7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide (1.0 g, 2.417 mmol) in THF was added. The reaction was warmed up to RT and stirred for an hour. The reaction was quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic phase was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography with gradient of 15-50% EtOAc/Hexane. The resulting material was dissolved in dry MeOH 10 mL and cooled in an ice bath. Hydrochloric acid, 4.0M solution in 1,4-dioxane (20 mL, 80 mmol) was added and mixture was stirred at RT for 4 h. The reaction was quenched with 10% sodium carbonate solution and extracted with DCM three times. The combined organic layers were washed with brine, dried on sodium sulfate, filtered and concentrated to give the desired product which was used without further purificationMS m/z=402.8 [M+H]+.

Provenance & Evidence