Sodium Hydroxide → HCID 86721349, compound

Participants

Reaction Steps

[step 4] (E)-2-(3-fluoro-8-{[4-methoxy-2-(methoxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (1.0 g, 2.1 mmol) obtained in step 3 was dissolved in dichloromethane (11 mL), boron tribromide (21.0 mL, 21.0 mmol, 1.0 mol/L dichloromethane solution) was added at 0° C., and the mixture was stirred at room temperature for 2 hr. To the mixture was added 2 mol/L aqueous sodium hydroxide solution, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v) to give (E)-2-(3-fluoro-8-{[4-hydroxy-2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (0.7 g, 75%).

Provenance & Evidence