[Li+].[BH4-].Cl[Si](C)(C)C.[CH3:8][N:9]([CH3:25])[C:10]1[C:15](/[CH:16]=[CH:17]/[N+:18]([O-])=O)=[CH:14][CH:13]=[C:12]([C:21]([F:24])([F:23])[F:22])[N:11]=1>C1COCC1>[NH2:18][CH2:17][CH2:16][C:15]1[C:10]([N:9]([CH3:8])[CH3:25])=[N:11][C:12]([C:21]([F:22])([F:23])[F:24])=[CH:13][CH:14]=1LiBH4 (13.3 mg, 0.613 mmol) was diluted with THF (1 mL) followed by the dropwise addition of chlorotrimethylsilane (155 μl, 1.23 mmol). After stirring for 15 minutes, argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction. (E)-N,N-dimethyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridin-2-amine (40 mg, 0.153 mmol) was added (in 500 μL of THF, gas evolution occurred). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (300 μl). The reaction mixture was concentrated, diluted with DCM and 20% KOH. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield the desired compound (20 mg, 0.0858 mmol, 56.0% yield).
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