Hydrogen Bromide → 3-(3-tert-Butyl-4-difluoromethoxy-phenyl)-1H-pyridin-2-one

HRID 2390792Notes

Reaction equation

HRID 2390792 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[C:16]([O:21]C)=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([F:14])[F:13])([CH3:4])([CH3:3])[CH3:2].Br>CC(O)=O>[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[C:16](=[O:21])[NH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([F:13])[F:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 670700073-(3-Tert-butyl-4-difluoromethoxy-phenyl)-2-methoxy-pyridine

Product 1

HCID 446250623-(3-tert-Butyl-4-difluoromethoxy-phenyl)-1H-pyridin-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

step 3—A mixture of 22 (82 mg, 0.267 mmol), 48% HBr (90 □L, 0.784 mmol) and HOAc (4 mL) in a sealed tube was heated overnight at 70° C. The reaction mixture was carefully poured into a cold sat'd. aq. NaHCO3 solution, and then extracted with EtOAc. The organic layer was washed with brine dried (Na2SO4), filtered and concentrated. The crude residue was purified by preparative TLC plate developed with 66% EtOAc in hexanes to afford 39 mg (50% yield) of 1-6 as a light yellow solid.

Workup

  1. additionThe reaction mixture was carefully poured into a cold sat'd
  2. extractionaq. NaHCO3 solution, and then extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by preparative TLC plate

Sources & evidence

ORD record
ord-9c4a37af0296487fae688332c2f79fd6
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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