Tert-Butylamine → 4-Bromo-2-(t-butylamino)-5-chloro-3,6-difluoropyridine

HRID 610220Notes

Reaction equation

HRID 610220 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[C:6](F)[N:5]=[C:4]([F:10])[C:3]=1[Cl:11].[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>C(#N)C>[Br:1][C:2]1[C:3]([Cl:11])=[C:4]([F:10])[N:5]=[C:6]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 221212794-Bromo-3-chloro-2,5,6-trifluoropyridine

Product 1

HCID 221211704-Bromo-2-(t-butylamino)-5-chloro-3,6-difluoropyridineYield 103.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 40 ml of acetonitrile was dissolved 10.2 g of 4-bromo-3-chloro-2,5,6-trifluoropyridine and 10.5 g of t-butylamine, and the mixture was heated under reflux for 1 hour and the solvent and the like were distilled off under reduced pressure. To the residue was added 80 ml of chloroform and the mixture was washed with 50 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 12.8 g of the title compound as reddish orange oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. distillationthe solvent and the like were distilled off under reduced pressure
  4. additionTo the residue was added 80 ml of chloroform
  5. washthe mixture was washed with 50 ml of distilled water
  6. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87af505b8e9a475690822ec90b895d08
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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