Hydrogen Bromide → 4-chloro-2,5-difluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide

HRID 1053167Notes

Reaction equation

HRID 1053167 reaction equation
[Cl:1][C:2]1[C:18]([F:19])=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([O:15]C)[CH:10]=2)=[O:7])=[C:4]([F:20])[CH:3]=1.Br.O>CC(O)=O>[Cl:1][C:2]1[C:18]([F:19])=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=2)=[O:7])=[C:4]([F:20])[CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 867284804-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide

Product 1

HCID 867284814-chloro-2,5-difluoro-N-(2-oxo-1H-pyridin-4-yl)benzamideYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
90 °C

Procedure

To 4-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide (3 g, 10.04 mmol) in HOAc (15.9 mL) was added HBr 33% in HOAc (12.31 mL of 33% w/v, 50.20 mmol) and the mixture was stirred at 90° C. for 5 h. Additional HBr (10 mL, 33% in HOAc) was added and the mixture was stirred at 90° C. overnight. The mixture was cooled to room temperature and was poured into water (100 mL). The mixture was stirred and the solid was collected by filtration. The solid was washed with water (2×50 mL). The solid was slurried in hexanes (2×50 mL) and filtered to give 4-chloro-2,5-difluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide (969.7 mg, 34%) as a cream colored solid. ESI-MS m/z calc. 284.02. found 285.3 (M+1)+; Retention time: 1.36 minutes (3 min run).

Workup

  1. stirringthe mixture was stirred at 90° C. overnight
  2. temperatureThe mixture was cooled to room temperature
  3. stirringThe mixture was stirred
  4. filtrationthe solid was collected by filtration
  5. washThe solid was washed with water (2×50 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b15e393daca9491fb14550495679d421
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

Loading…