Acetic Acid → (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

HRID 1845854Notes

Reaction equation

HRID 1845854 reaction equation
CC(O)=O.CCO.[Br:8][C:9]1[CH:10]=[C:11]([O:18][C@@H:19]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[Cl:29])[CH3:20])[C:12]([N+:15]([O-])=O)=[N:13][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O.C(OCC)C>[Br:8][C:9]1[CH:10]=[C:11]([O:18][C@@H:19]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[Cl:29])[CH3:20])[C:12]([NH2:15])=[N:13][CH:14]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 681943985-Bromo-3-((1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Product 1

HCID 11689426(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amineYield 84%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of AcOH (150 mL) and EtOH (150 mL) was suspended 5-bromo-3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-nitropyridine (6.6 g, 0.016 mol) and iron chips (8.8 g, 0.16 mol). The reaction was heated slowly to reflux and allowed to stir for 1 hour. The reaction was cooled to room temperature then diethyl ether (100 mL) and water (100 mL) was added. The solution was carefully neutralized by the addition of sodium carbonate. The combined organic extracts were washed with saturated NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL) then dried over Na2SO4, filtered and concentrated to dryness under vacuum to yield the title compound as a white solid (5.0 g, 84%).

Workup

  1. temperatureThe reaction was heated slowly
  2. temperatureto reflux
  3. washThe combined organic extracts were washed with saturated NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL)
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-e816cfbe9b544f33951e70d5ede58558
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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