F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[S:15][CH:16]=[CH:17][C:18]=1[C:19]#[N:20].[H-].[Na+]>C1COCC1>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([NH:13][C:14]2[S:15][CH:16]=[CH:17][C:18]=2[C:19]#[N:20])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1Combine 2,4,5-trifluoro-nitrobenzene (5.00 g, 24.24 mmol), 2-aminothiophene-3-carbonitrile (3.51 g, 28.24 mmol), and anhydrous THF (30.0 ml). Cool the mixture to 10° and then slowly add NaH (2.26 g, 56.47 mmol, 60% dispersion in mineral oil) while keeping the temperature less than 10°. Warm the mixture to ambient temperature after NaH addition is complete. Stir the mixture at ambient temperature for 24 hours and then pour it onto ice chips. Extract the aqueous with ethyl acetate and then wash (brine), dry (sodium sulfate), and reduce the organic to residue. Purify the residue on silica gel using hexanes/dichloromethane (35:65) to give 4.06 g (51%) of the title compound as a red solid: mass spectrum (ion spray): m/z=280.0 (M−1).
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