Sodium Azide → Ethyl 3-(azidomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

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A mixture of 1.14 g of ethyl 3-(bromomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 19) and 337 mg of sodium azide in 6 mL of DMF is stirred at room temperature for 3 h, then diluted slowly with water to a volume of 50 ml. The resulting solid is filtered, washed well with water, and dried in vacuo to afford 759 mg of the title compound as a cream colored solid. Recrystallization of a sample from acetonitrile gives tan needles.

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