Stannous Chloride → 3-amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide
Reaction equation
[F:1][C:2]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[C:18]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15]([O:16][CH3:17])=[N:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:22][C:21]1[C:2]([F:1])=[C:3]([C:18]([F:25])=[CH:19][CH:20]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15]([O:16][CH3:17])=[N:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5]Participants
4
Procedure
2,6-Difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-nitrobenzamide (762.3 mg, 2.183 mmol) was dissolved in ethyl acetate (21.8 mL) and treated with tin (II) chloride dehydrate (2463 mg, 10.91 mmol). The reaction mixture was heated to reflux for 2 hours and then allowed to cool to ambient temperature. The reaction mixture was quenched with saturated sodium carbonate and filtered. The filtrate was washed with water (2×), sodium bicarbonate (2×), and brine (1×), dried over sodium sulfate, and concentrated to afford 3-amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (588.2 mg, 1.842 mmol, 84.4% yield) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.629-12.519 (s, 1H), 10.980-10.883 (s, 1H), 8.675-8.583 (s, 1H), 8.544-8.458 (s, 1H), 6.993-6.811 (m, 2H), 5.297-5.188 (s, 2H), 4.093-3.973 (s, 3H); MS (APCI-pos) m/z=320.3 (M+H).