HCID 22277998, compound → HCID 10251314, compound

HRID 1064091Notes

Reaction equation

HRID 1064091 reaction equation
[CH:1]1([CH2:7][N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:11]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[C:10](=[O:27])[N:9]2[CH3:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-].[Br-].[Br-].C1([N+](CC)(CC)CC)C=CC=CC=1.C1([N+](CC)(CC)CC)C=CC=CC=1.C1([N+](CC)(CC)CC)C=CC=CC=1>C1(C)C=CC=CC=1.CN(C=O)C>[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[C:10](=[O:27])[N:9]2[CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 22277998HCID 22277998, compoundHCID 86591495Phenyltriethylammonium tribromide

Product 1

HCID 10251314HCID 10251314, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

The solution of 1-Cyclohexylmethyl-4-(3,4-dichloro-phenyl)-2-methyl-5-pyridin-4-yl-pyrazolidin-3-one 0.16 g in toluene 20 mL and DMF 2 mL was treated with phenyltriethylammonium tribromide 0.22 g at room temperature, The reaction mixture was refluxed for 4 h. The reaction was quenched with sat. Na2SO3 25 mL at 0° C. The reaction mixture was extracted with dichloromethane, 3×25 mL. The combined organic phase was washed with brine, dried over anhydrous Na2SO4. After purification by flash chromatography, the title compound was obtained as light yellow solid 80 mg. MS (ES+): 416 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customThe reaction was quenched with sat. Na2SO3 25 mL at 0° C
  3. extractionThe reaction mixture was extracted with dichloromethane, 3×25 mL
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-4858e7d5a61b446d9d75be7622323e50
Source dataset
uspto-grants-2005_11
Patent number
US06967254B2

Reaction notes

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