Water → 4-(4-Bromo-2-fluorophenylamino)-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid

HRID 422787

反応式

HRID 422787 の反応式
C[O:2][C:3]([C:5]1[C:10](Cl)=[CH:9][C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1)=[O:4].[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([F:27])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>ClC1C=CC=CC=1Cl.CCOC(C)=O>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:10]2[C:5]([C:3]([OH:2])=[O:4])=[N:6][N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[CH:9]=2)=[C:22]([F:27])[CH:21]=1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230504-Bromo-2-fluoroanilineHCID 2784479Methyl 4-chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylate

生成物 1

HCID 666739604-(4-Bromo-2-fluorophenylamino)-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid収率 43%

試薬・触媒・溶媒 2

HCID 72391,2-Dichlorobenzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 4-chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid methyl ester (0.250 g, 0.944 mmol) in 1,2-dichlorobenzene (3.8 mL) was added 4-bromo-2-fluoro aniline (0.561 g, 3.78 mmol), and cesium carbonate (0.615 mg, 1.89 mmol). The reaction mixture was heated to reflux. After 1 hour, the reaction mixture was cooled to room temperature. Water was added and the mixture was diluted with EtOAc. The aqueous layer was separated, acidified with 10% HCl solution, and extracted with EtOAc. The combined organic layers were dried (MgSO4), concentrated under reduced pressure, and triturated to give 0.153 g (43%) of the desired product.

後処理

  1. temperatureThe reaction mixture was heated to reflux
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customtriturated

出典と根拠

ORDレコード
ord-4f12d9af575848a48fc4f4b09c0c72fd
出典データセット
uspto-grants-2012_01
特許番号
US08101639B2

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