Ammonia → 1-prop-2-ynylbenzimidazole

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Reaction Steps

To a solution of 1H-benzimidazole (1.0 g, 8.46 mmol) in N,N-dimethylformamide (12 mL) was added a 1M solution of potassium tert-butoxide in tetrahydrofuran (8.04 mL, 8.04 mmol). The solution was stirred at room temperature for about 10 min, before propargyl bromide (0.940 mL, 8.46 mmol) was added dropwise. The solution was stirred at room temperature for about 30 min, poured into a cooled saturated aqueous solution of sodium bicarbonate and was extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated under vacuum to provide Example 648. MS (DCI-NH3): m/z 157 (M+H)+.

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