[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-fluorophenyl)-methanone → [2-Amino-5-(4-fluorobenzoyl)phenyl](3-chlorophenyl)-methanone

HRID 1788041Notes

Reaction equation

HRID 1788041 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[O:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1>C1COCC1.O>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:18])[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:13][C:12]=1[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:9]

Participants

4

Reactant 1

HCID 17976104[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-fluorophenyl)-methanone

Product 1

HCID 17976107[2-Amino-5-(4-fluorobenzoyl)phenyl](3-chlorophenyl)-methanoneYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate 2 (0.0514 mol) in THF (180 ml) was cooled on an ice bath. TiCl3 15% in water (180 ml) was added dropwise slowly. The mixture was stirred at room temperature overnight, then poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 18.2 g (100%) of [2-amino-5-(4-fluorobenzoyl)phenyl](3-chlorophenyl)-methanone (intermediate 3).

Workup

  1. temperaturewas cooled on an ice bath
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-233e49deed1b4a17ba42f269f2354d5e
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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