[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-])=O.Cl.O.O.[Sn](Cl)Cl.[OH-].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[NH2:9]4-Bromo-2-methyl-3-nitropyridine (1.2 g, 5.53 mmol) was dissolved in HCl (2.189 ml, 26.3 mmol), tin(II)chloride dihydrate (4.99 g, 22.12 mmol) was added and stirred at 40° C. for 1 hour. The reaction mixture was made basic with 30% NaOH (18 mL), extracted with EtOAc, dried over sodium sulfate and concentrated under vacuum to give a yellow oil. The oil was further dried under high vacuum for 4 hours to give 4-bromo-2-methylpyridin-3-amine (1 g, 5.35 mmol, 97% yield) which was stored at −17° C. until use and was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.26-2.42 (3H, m) 5.05-5.34 (2H, m) 7.17-7.32 (1H, m) 7.46-7.64 (1H, m). MS [M+H] found 187.0.
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