Potassium Carbonate → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)-2-(tetrahydropyran-4-yl)methylbenzimidazole

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Reaction Steps

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (250 mg, 0.808 mmol) in dimethylformamide (3 mL) was added (4-tetrahydropyranyl)acetaldehyde (114 mg, 0.889 mmol) and oxone (323 mg, 0.525 mmol), and this was stirred at room temperature for 2 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (197 mg, 58% yield) as light brown crystals.

Provenance & Evidence