Sodium Iodide → 8-(2-tert-Butoxycarbonylamino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

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Reaction Steps

5.5 g of sodium iodide and 8.0 g of sodium carbonate are added at RT to a solution of 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (4.8 g) and 2-tert-butoxycarbonylamino-6-methylbenzyl chloride (9.2 g) in acetone (250 ml) and the mixture is then heated to boiling under reflux for 6 h. After cooling the solution to RT and concentrating it, the residue is dissolved in a mixture of 200 ml of ethyl acetate and 200 ml of water and the organic phase is separated off. After three further extractions with 100 ml each of ethyl acetate, the combined organic phases are dried over magnesium sulfate and then concentrated. The title compound crystallizes as a slightly yellow solid. After chromatographic purification on silica gel (eluent: toluene/dioxane=20:1) and recrystallization from diisopropyl ether, 7.1 g (62%) of the title compound of m.p. 149-152° C. are obtained.

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