Benzyl Alcohol → 8-(Benzyloxy)-6-bromo-2,3-dimethylimidazo[1,2-a]pyridine

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Reaction Steps

With ice-cooling, 34.8 ml of benzyl alcohol are added dropwise to a suspension of 13.5 g of sodium hydride (60% suspension in paraffin) in 510 ml of dimethylformamide, and the mixture is stirred for 1 h until the evolution of gas has ceased. 51.2 g of 6,8-dibromo-2,3-dimethylimidazo[1,2-a]pyridine are then introduced in small portions, and the mixture is stirred at room temperature for 40 h. The mixture is then poured into 1 l of ice-water and extracted three times with in each case 100 ml of dichloromethane, the combined organic extracts are washed with saturated aqueous ammonium chloride solution and twice with water and concentrated to dryness under reduced pressure, and the residue is triturated with a little ethyl acetate. The resulting precipitate is filtered off and dried under reduced pressure. This gives 43.2 g of the title compound of m.p. 151–3° C. (ethyl acetate).

Provenance & Evidence