Water → HCID 69331807, compound

HRID 351234Notes

Reaction equation

HRID 351234 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[N:16]=[C:15]([O:26][CH3:27])[CH:14]=2)=[CH:9][CH:8]=1)(=O)=O.CCOC(C)=O.O.[CH3:37][N:38](C=O)C>[C-]#N.[Zn+2].[C-]#N.[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>[CH3:27][O:26][C:15]1[CH:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:37]#[N:38])=[CH:8][CH:9]=2)[N:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 21090947HCID 21090947, compound

Product 1

HCID 69331807HCID 69331807, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
85 °C

Procedure

A mixture of 4-[3-methoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenyl trifluoromethanesulfonate (679 mg), zinc cyanide (279 mg), and tetrakis(triphenylphosphine)-palladium(0) (183 mg) in DMF (4 ml) was stirred at 85° C. for 5 hours. The reaction mixture was cooled to ambient temperature and AcOEt and H2O were added. Unsoluble matter was filtered off through a celite pad. The filtrate was partitioned, and the organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated invacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=20%. The pure fractions were collected and concentrated in vacuo to give 4-[3-methoxy-1-(4-methoxy-phenyl) -1H-pyrazol-5-yl]benzonitrile (326 mg) as a powder.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationUnsoluble matter was filtered off through a celite pad
  3. customThe filtrate was partitioned
  4. washthe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated invacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with AcOEt/n-hexane=20%
  9. customThe pure fractions were collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a032611b1f4406a9da5cb6a23202ec2
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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