Stannous chloride dihydrate → 5-Bromo-6'-methoxy-2,3'-bipyridin-3-amine

HRID 1431564Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred mixture of 5-bromo-6′-methoxy-3-nitro-2,3′-bipyridine (776.9 mg, 2.50 mmol) in EtOAc (25 mL) was added tin(II) chloride dihydrate (2.83 g, 12.56 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 90° C. After 2 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate, filtration, and concentration, the light tan solid was identified as 5-bromo-6′-methoxy-2,3′-bipyridin-3-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.42 (1H, dd, J=2.4, 0.7 Hz), 7.98 (2H, m), 7.34 (1H, d, J=2.0 Hz), 6.90 (1H, dd, J=8.6, 0.7 Hz), 5.49 (2H, s), 3.90 (3H, s).

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, filtration, and concentration

Sources & evidence

ORD record: ord-d6caa3bda7074914bf76eb297489ee81
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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