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

HRID 1053167
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HRID 1053167 반응식
[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
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참가 물질

5

반응물 3

HCID 260Hydrogen Bromide2회HCID 962WaterHCID 867284804-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b15e393daca9491fb14550495679d421
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09393235B2

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