Cesium carbonate → HCID 86721355, compound

Participants

Reaction Conditions

Reaction Steps

[step 2] (E)-2-[8-({2-[(tert-butyldimethylsiloxy)methyl]-4-hydroxy-1H-benzo[d]imidazol-1-yl}methyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (200 mg, 0.36 mmol) obtained in step 1 was dissolved in DMF (5.5 mL), cesium carbonate (352 mg, 1.08 mmol) and sodium 2-chloro-2,2-difluoroacetate (165 mg, 1.08 mmol) were added, and the mixture was stirred at 60° C. for 1 hr. To the mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-20/80 v/v) to give (E)-2-(8-{[4-(difluoromethoxy)-2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (55 mg, 31%).

Provenance & Evidence