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Potassium Carbonate → 2,5-Difluoro-N-(methylsulfonyl)-4-[(6-nitropyridin-3-yl)oxy]benzamide

HRID 2048014
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HRID 2048014 반응식
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:20]=[C:19]([OH:21])[C:18]([F:22])=[CH:17][C:9]=1[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11].Br[C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[N:28][CH:29]=1>CS(C)=O>[F:7][C:8]1[CH:20]=[C:19]([O:21][C:24]2[CH:29]=[N:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:18]([F:22])=[CH:17][C:9]=1[C:10]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])=[O:11]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridineHCID 580424162,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide

생성물 1

HCID 580424052,5-Difluoro-N-(methylsulfonyl)-4-[(6-nitropyridin-3-yl)oxy]benzamide수율 60.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Potassium carbonate (0.220 g, 1.59 mmol) was added to a stirred solution of 2,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide (Preparation 34, 0.200 g, 0.796 mmol) and 5-bromo-2-nitropyridine (0.170 g, 0.836 mmol) in DMSO (2.5 mL) at room temperature. The mixture was stirred at room temperature for 2 hours and then at 60° C. for 24 hours. The reaction mixture was partitioned between EtOAc and 2M aqueous HCl ensuring the water layer was acidic. The organic layer was separated and washed further with citric acid, water and brine, then dried over magnesium sulfate, filtered, evaporated in vacuo and triturated in diethyl ether to yield the title compound (0.180 g, 60%):

후처리

  1. waitat 60° C. for 24 hours
  2. customThe reaction mixture was partitioned between EtOAc and 2M aqueous HCl ensuring the water layer
  3. customThe organic layer was separated
  4. washwashed further with citric acid, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customtriturated in diethyl ether

출처 및 근거

ORD 기록
ord-84bfbdc7f1c34a1f89d326dfcb32db1b
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592629B2

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