Stannous chloride dihydrate → 4-Bromo-6-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-3-amine

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Reaction Conditions

Reaction Steps

To a mixture of 4-bromo-5-nitro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridine (50 mg, 0.160 mmol) in EtOH (10 mL) was added tin(II) chloride dihydrate (180 mg, 0.799 mmol). The mixture was stirred at 85° C. for 16 h. Then the mixture was added to an aqueous NaHCO3 solution. The mixture was extracted with EA (50 mL×2). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative TLC (PE/EA=2:1, Rf=0.5) to yield a light yellow solid of 4-bromo-6-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-3-amine (30 mg, 0.090 mmol, 56.4% yield): 1H NMR (400 MHz, CD3OD): δ 8.05 (s, 1H), 7.58 (s, 1H), 1.56 (s, 6H). ES-LCMS m/z 283.1 (M+H).

Provenance & Evidence