Trifluoroacetic acid → (4-Bromo-2-fluorophenyl)[4-(3-chloro-5-methylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804058Notes

Reaction equation

HRID 1804058 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+].[Br:31][C:32]1[CH:40]=[CH:39][C:35](C(Cl)=O)=[C:34]([F:41])[CH:33]=1>C(Cl)(Cl)Cl>[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:6]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=3)[CH2:12][CH2:13]2)=[O:7])=[C:34]([F:41])[CH:33]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 27340264-Bromo-2-fluorobenzoyl chlorideHCID 673809194-(3-Chloro-5-methylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58484756(4-Bromo-2-fluorophenyl)[4-(3-chloro-5-methylpyridin-2-yl)piperazin-1-yl]methanoneYield 102.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(3-Chloro-5-methylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (1.4 g), which is the intermediate described in Preparation Example 48, was dissolved in chloroform (2.5 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was alkalified with 1N aqueous sodium hydroxide solution, and extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. By reaction and treatment in the same manner as in Preparation Example 8 and using the obtained residue and 4-bromo-2-fluorobenzoyl chloride (1.1 g), the title compound (1.9 g) was obtained.

Workup

  1. customdescribed in Preparation Example 48
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customBy reaction and treatment in the same manner
  6. customas in Preparation Example 8

Sources & evidence

ORD record
ord-b50f80faad024fe49aa2f14889088a26
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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