Water → HCID 22261035, compound

HRID 503156Notes

Reaction equation

HRID 503156 reaction equation
Br[C:2]1[C:3]([O:18][CH3:19])=[CH:4][C:5]([F:17])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[O:9])[CH:7]=1.O.[CH3:21][N:22](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:17][C:5]1[C:6]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:7][C:2]([C:21]#[N:22])=[C:3]([O:18][CH3:19])[CH:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 22260993(5-Bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanone

Product 1

HCID 22261035HCID 22261035, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

A total of 856 mg of (5-bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanone obtained in Production Example II-1-b was dissolved in 13.1 ml of N,N-dimethylformamide, 185 mg of zinc cyanide, 13.6 mg of tris(dibenzylideneacetone)dipalladium and 17.4 mg of 1,1′-bis(diphenylphosphino)ferrocene were added thereto, and the mixture was stirred at 120° C. in an atmosphere of nitrogen gas for 7 hours. After cooling to room temperature, water was added to the reaction mixture and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:2), to give 203 mg of the title compound as pale yellow crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-17c956c663db43bc8530f0c5a52c71f6
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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