[CH:1]1([C:4]2[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N+:12]([O-])=O)=[CH:6][N:5]=2)[CH2:3][CH2:2]1.CO.[BH4-].[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+].O.[Ni](Cl)Cl>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([NH2:12])=[C:8]([O:10][CH3:11])[CH:9]=2)[CH2:3][CH2:2]1To a mixture of 2-cyclopropyl-4-methoxy-5-nitropyridine (805 mg, 4.15 mmol), nickel(II) chloride, 6H2O (2956 mg, 12.44 mmol), and methanol (25 mL), cooled to 0° C., was added sodium borohydride (941 mg, 24.87 mmol) portion wise over 1 minute. After 5 minutes, the reaction was diluted with DCM (50 mL), saturated sodium bicarbonate (50 mL), and water (50 mL), and filtered through Celite©. The layers of the filtrate were separated and the aqueous layer was further extracted with DCM (50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), eluted through a phase separator, and concentrated to afford 6-cyclopropyl-4-methoxypyridin-3-amine (448 mg, 63%) as a yellow oil. MS (m/z) 165.1 (M+H+).
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