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

HRID 1817964Notes

Reaction equation

HRID 1817964 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 72391,2-DichlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7146fa075f09425f8d4f399cd940b401
Source dataset
uspto-grants-2009_10
Patent number
US07598383B2

Reaction notes

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