Stannous chloride dihydrate → HCID 59631173, compound

HRID 1431543Notes

Reaction equation

HRID 1431543 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:17]([O-])=O)[C:5]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]([O:15][CH3:16])[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]([NH2:17])[C:5]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]([O:15][CH3:16])[CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59631198HCID 59631198, compound

Product 1

HCID 59631173HCID 59631173, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of 5-bromo-5′-fluoro-2′-methoxy-3-nitro-2,4′-bipyridine (0.22 g, 0.67 mmol) in EtOAc (15 mL) was added tin(II) chloride dihydrate (0.76 g, 3.37 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 purified on basic alumina (0-15% EtOAc in hexanes) to afford a residue as 5-bromo-5′-fluoro-2′-methoxy-2,4′-bipyridin-3-amine. 1H NMR (500 MHz, CDCl3) δ ppm 8.19 (1H, d, J=2.0 Hz), 8.13 (1H, d, J=1.5 Hz), 7.29 (1H, d, J=2.0 Hz), 6.89 (1H, d, J=4.9 Hz), 3.95 (3H, s).

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
  5. customthe residue was purified on basic alumina (0-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-66087ff4030a4460a5b4b5372f7a71e1
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…