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

HRID 2048014
ノート
印刷プレビュー

反応式

HRID 2048014 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%):

後処理

  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

出典と根拠

ORDレコード
ord-84bfbdc7f1c34a1f89d326dfcb32db1b
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592629B2

反応ノート

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