[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:19]=3[CH3:27])[C:8]=2[C:9](Cl)=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH4+].[Cl-]>O1CCOCC1.C1COCC1.CN(C=O)C.O.C(OCC)(=O)C.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:19]=3[CH3:27])[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])[CH3:2]To a stirred solution of 4-chloro-3-(2-methyl-5-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (815.2 mg, 2.00 mmol) (from Example 22 supra) in 1,4-dioxane (40 mL), THF (20 mL) and DMF (20 mL) was added NH4Cl (1.59 mg, 29.6 mmol) in water (12 mL). Zinc powder (948 mg, 14.5 mmol) was then added in several portions and the reaction was stirred at room temperature for a total of 4 hours. The resulting mixture was diluted with ethyl acetate (800 mL), washed with water (100 mL) and then brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 95/5) to give 3-(5-amino-2-methyl-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 584 mg, 85%).
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