O.O.[Sn](Cl)Cl.[CH3:6][C:7]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([N+:21]([O-])=O)=[CH:13][N:12]=1)([CH3:10])[C:8]#[N:9].[OH-].[Na+]>CC(=O)OCC>[NH2:21][C:14]1[CH:15]=[C:16]([C:17]([F:20])([F:18])[F:19])[C:11]([C:7]([CH3:10])([CH3:6])[C:8]#[N:9])=[N:12][CH:13]=1Tin(II) chloride dihydrate (449 mg, 1.991 mmol) was added to a solution of 2-methyl-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)propanenitrile (129 mg, 0.498 mmol) in EA (15 mL). The mixture was at 60° C. for 4 h. Then the solution was adjusted to pH=8-9 with 2N NaOH. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative HPLC (MeCN/H2O as eluants, basic condition) to yield a white solid of 2-(5-amino-3-(trifluoromethyl)pyridin-2-yl)-2-methylpropanenitrile (46.48 mg, 0.203 mmol, 40.7% yield). TLC (PE/EA=1:1, Rf=0.3): 1H NMR (400 MHz, DMSO-d6) δ 8.04-8.17 (m, 1H), 7.31 (d, J=2.43 Hz, 1H), 5.97 (s, 2H), 1.70 (s, 6H); ES-LCMS m/z 230.1 (M+H).
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