Sodium Bicarbonate → 5-(Benzoxazol-2-yl)-2-(3-methoxyphenyl)-1-(tetrahydropyran-4-yl)benzimidazole

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Reaction Steps

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in methanol (5 mL) was added ethyl 3-methoxybenzimidate hydrochloride (153 mg, 0.711 mmol), and this was stirred at room temperature for 8 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The crystals obtained were purified by silica gel column chromatography to yield the title compound (216 mg, 79% yield) as light brown crystals.

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