2-Methylphenyl boronic acid → HCID 18322307, compound

HRID 1698872Notes

Reaction equation

HRID 1698872 reaction equation
[OH-].[Ba+2].[OH-].[C:4]1([CH3:13])[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O.[Cl:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[C:23]1[N:24]=[C:25]([N:29]([C:33]2[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:34]=2[O:40][CH3:41])[CH2:30][CH2:31][CH3:32])[S:26][C:27]=1[CH3:28]>C(O)C.O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Cl:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[C:23]1[N:24]=[C:25]([N:29]([C:33]2[CH:38]=[C:37]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH3:13])[CH:36]=[CH:35][C:34]=2[O:40][CH3:41])[CH2:30][CH2:31][CH3:32])[S:26][C:27]=1[CH3:28]

Participants

7

Reactant 3

HCID 27332672-Methylphenyl boronic acidHCID 6093286Barium hydroxideHCID 18322261HCID 18322261, compound

Product 1

HCID 18322307HCID 18322307, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.96 g of barium hydroxide, 0.52 g of o-tolyl-boronic acid and 40 mg of palladium diacetate are added in succession to 1 g of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-bromo-2-methoxyphenyl)-N-propylamino]thiazole, in solution in 25 ml of ethanol and 0.8 ml of water. The reaction mixture is heated for 1 hour under reflux; after returning to room temperature, it is filtered on Celite. After evaporation of the solvent, the residue is taken up in dichloromethane. The organic phase is washed with water and then dried over sodium sulphate. The evaporation residue is purified on silica gel; eluent dichloromethane/cyclohexane 9/1 (v/v). The expected product is obtained in the form of a powder; m.p.=55° C.

Workup

  1. temperatureThe reaction mixture is heated for 1 hour
  2. temperatureunder reflux
  3. customafter returning to room temperature
  4. filtrationit is filtered on Celite
  5. customAfter evaporation of the solvent
  6. washThe organic phase is washed with water
  7. dry with materialdried over sodium sulphate
  8. customThe evaporation residue is purified on silica gel

Sources & evidence

ORD record
ord-088b139ba3dc43898e812705bc4ea4d1
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

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