Methanol → 2-(t-Butylamino)-5-chloro-3,6-difluoropyridine

HRID 1274710Notes

Reaction equation

HRID 1274710 reaction equation
CO.Br[C:4]1[C:9]([Cl:10])=[C:8]([F:11])[N:7]=[C:6]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[F:17]>[Pd].C(N(CC)CC)C>[C:13]([NH:12][C:6]1[C:5]([F:17])=[CH:4][C:9]([Cl:10])=[C:8]([F:11])[N:7]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 887MethanolHCID 221211704-Bromo-2-(t-butylamino)-5-chloro-3,6-difluoropyridine

Product 1

HCID 221211892-(t-Butylamino)-5-chloro-3,6-difluoropyridineYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To 30 ml of methanol were added 12.8 g of 4-bromo-2-(t-butylamino)-5-chloro-3,6-difluoropyridine and 2.5 g of triethylamine together with 0.57 g of 10% palladium on carbon, and the mixture was hydrogenated at 50° C. for 5 days. The catalyst was separated by filtration, 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 70 ml of distilled water, and the chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 9.3 g of the title compound as a brown oil.

Workup

  1. customThe catalyst was separated by filtration
  2. distillationthe solvent and the like were distilled off under reduced pressure
  3. additionTo the residue was added 80 ml of chloroform
  4. washthe mixture was washed with 70 ml of distilled water
  5. dry with materialthe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd5aa83f6ff24021a774203de67e4f55
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

Loading…