Hydrogen Bromide → HCID 86728478, compound

HRID 1053164Notes

Reaction equation

HRID 1053164 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13]C)[CH:8]=1)=[O:5].Br.O>C(O)(=O)C>[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 86728477HCID 86728477, compound

Product 1

HCID 86728478HCID 86728478, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
90 °C

Procedure

To 2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide (2.60 g, 9.84 mmol) in acetic acid (15.60 mL) was added HBr 33% in acetic acid (12.1 mL of 33% w/v, 49.20 mmol) and the mixture was stirred at 90° C. for 5 h. Additional HBr (10 mL, 33% in acetic acid) was added and the mixture was stirred at 90° C. overnight. The mixture was cooled to room temperature and was poured into water (200 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 2,5-difluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide (2.30 g, 9.19 mmol, 93%). ESI-MS m/z calc. 250.05. found 251.3 (M+1)+; Retention time: 1.16 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 11.31 (s, 1H), 10.59 (s, 1H), 7.56 (ddd, J=8.2, 5.4, 3.0 Hz, 1H), 7.46 (pd, J=9.1, 4.4 Hz, 2H), 7.33 (d, J=7.2 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.42 (dd, J=7.2, 2.1 Hz, 1H) ppm.

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-e301bf55800647318f499da84726e08a
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

Loading…