Hydrochloric Acid → 5-[(2-chloro-4-fluorophenyl)acetyl]-1-(2,6-dichlorophenyl)pyridin-2(1H)-one

HRID 2235044Notes

Reaction equation

HRID 2235044 reaction equation
BrCCBr.[Cl:5][C:6]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:7]=1[CH2:8]Br.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[N:23]1[C:28](=[O:29])[CH:27]=[CH:26][C:25]([C:30](Cl)=[O:31])=[CH:24]1.Cl>[Zn].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.COCCOC>[Cl:5][C:6]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:7]=1[CH2:8][C:30]([C:25]1[CH:26]=[CH:27][C:28](=[O:29])[N:23]([C:17]2[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=2[Cl:15])[CH:24]=1)=[O:31]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneHCID 866164541-(2,6-Dichlorophenyl)-6-oxo-1,6-dihydropyridine-3-carbonylchloride

Product 1

HCID 666701395-[(2-chloro-4-fluorophenyl)acetyl]-1-(2,6-dichlorophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of zinc powder (208 mg) and ethylene glycol dimethyl ether (10 mL) were added 1,2-dibromoethane (20 mg) and 2-chloro-4-fluorobenzyl bromide (473 mg) and the mixture was stirred at 75° C. for 1 hour. The compound prepared in Example 5 and tetrakis(triphenylphosphine)-palladium (123 mg) were added hereto and the reaction mixture was stirred at same temperature for 15 minutes. The reaction mixture was added by hydrochloric acid (1 mol/L) and ethyl acetate, then the water layer was extracted with ethyl acetate. The obtained extract was dried with anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give the title compound (171 mg) having the following physical data.

Workup

  1. stirringthe reaction mixture was stirred at same temperature for 15 minutes
  2. extractionthe water layer was extracted with ethyl acetate
  3. extractionThe obtained extract
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d8666a7e771b4745ae9ad15768c9e28f
Source dataset
uspto-grants-2010_05
Patent number
US07713998B2

Reaction notes

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