Stannous chloride dihydrate → 5-Bromo-2-(3-methoxyphenyl)pyridin-3-amine

HRID 1431373Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:6][CH:7]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred mixture of 5-bromo-2-(3-methoxyphenyl)-3-nitropyridine (0.19 g, 0.61 mmol) in EtOAc (10 mL) was added tin(II) chloride dihydrate (0.70 g, 3.10 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 70° C. After 23 h, the reaction was cooled to rt and diluted with ethyl acetate, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The beige solid was identified as mostly 5-bromo-2-(3-methoxyphenyl)pyridin-3-amine. 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (1H, quin, J=1.6 Hz), 7.30 (1H, m), 7.12 (2H, m), 6.87 (1H, m), 3.96 (2H, br. s.), 3.72 (3H, t, J=1.4 Hz).

Workup

additionUpon complete addition of the reducing agent
temperaturethe reaction was cooled to rt
washwashed with 1M NaOH, water, and brine
dry with materialAfter drying over anhydrous sodium sulfate and filtration
customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-9033fb3644d64dedb1bf6ecaffa5b5f0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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