Br[CH2:2][C:3]1[C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:12])[C:6]=2[S:5][CH:4]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][C:3]1[C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:12])[C:6]=2[S:5][CH:4]=1)=[N+:20]=[N-:21]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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