Acetaldehyde → 2-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

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Reaction Steps

To a solution of 2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 46-2) (0.56 g, 1.7 mmol) in dimethylformamide (5 mL) containing water (0.18 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 90 mg, 1.8 mmol) and oxone (0.69 mg, 1.1 mmol), and this was stirred at room temperature for 3 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 (123 mg, 20.4% yield) as light brown crystals.

Provenance & Evidence