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

HRID 1431546Notes

Reaction equation

HRID 1431546 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

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 596310815-Bromo-2-(6-methoxypyridin-3-yl)-3-nitropyridine

Product 1

HCID 596314045-Bromo-6'-methoxy-2,3'-bipyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of 5-bromo-6′-methoxy-3-nitro-2,3′-bipyridine (0.34 g, 1.10 mmol) in EtOAc (10 mL) was added tin(II) chloride dihydrate (1.26 g, 5.57 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 70° C. After 19 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 residue was identified as mostly 5-bromo-6′-methoxy-2,3′-bipyridin-3-amine. 1H NMR (500 MHz, CDCl3) δ ppm 8.50 (1H, d, J=2.4 Hz), 8.18 (1H, d, J=2.0 Hz), 7.90 (1H, dd, J=8.6, 2.4 Hz), 7.26 (1H, m), 6.88 (1H, d, J=8.6 Hz), 4.07 (5H, m).

Workup

  1. additionUpon complete addition of the reducing agent
  2. temperaturethe reaction was cooled to rt
  3. washwashed with 1M NaOH, water, and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate, filtration, and concentration

Sources & evidence

ORD record
ord-121b100c4e9c4d94af1a3465a8765e17
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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