O.O.[Sn](Cl)Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[CH:9][C:8]=1[N+:23]([O-])=O.[OH-].[K+]>C(O)C.O1CCCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[CH:9][C:8]=1[NH2:23]Add tin (II) chloride dihydrate (1.41 g, 6.26 mmol) to a suspension of 3-(4-fluoro-3-nitrophenylethynyl)-5-methoxypyridine, (prepared as described in EXAMPLE 116), (190 mg, 0.69 mmol) in ethanol (20 mL) and tetrahydrofuran (17 mL) under nitrogen and heat at 70° C. for 2 h. Cool the reaction mixture, add a 50% aqueous solution of potassium hydroxide (100 mL), and extract with diethyl ether (2×100 mL). Wash the combined organic phases with an aqueous saturated solution of sodium chloride (100 mL), dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with ethyl acetate to give the title compound as a yellow solid. Further purify the title compound by silica gel chromatography, eluting with 100% dichloromethane to 20:80 ethyl acetate:dichloromethane, to give the title compound as a white solid (143 mg, 86%).
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