HCID 178418260, compound → HCID 178440448, compound

HRID 604410Notes

Reaction equation

HRID 604410 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH2:12][CH2:13][CH3:14])[C:10]=1I)=[O:5])[CH3:2].[Cu](C#N)[C:16]#[N:17]>[C-]#N.C([N+](CC)(CC)CC)C.CN(C=O)C.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]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH2:12][CH2:13][CH3:14])[C:10]=1[C:16]#[N:17])=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 178418260HCID 178418260, compoundHCID 178440449HCID 178440449, compound

Product 1

HCID 178440448HCID 178440448, compound

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1.5 g (4.9 mmol) of 4-Iodo-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester, 0.87 g (9.7 mmol) of copper cyanide and 404 mg (2.4 mmol) of tetraethylammonium cyanide were dissolved in 10 ml of DMF and 20 ml of tetrahydrofuran and the solution was degassed with argon. 223 mg (0.2 mmol) of Tris(dibenzylideneacetone)dipalladium (0) and 404 mg (0.7 mmol) of 1,1′-bis-(diphenylphosphino) ferrocene were added at RT. The reaction was stirred at 120° C. for 5 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and this solution was washed with saturated aqueous sodium bicarbonate. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography eluting with n-heptane:ethyl acetate/1:1.

Workup

  1. custom20 ml of tetrahydrofuran and the solution was degassed with argon
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthis solution was washed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by silica gel chromatography
  9. washeluting with n-heptane

Sources & evidence

ORD record
ord-05bf642ccd0e493ab7203a7b124a00de
Source dataset
uspto-grants-2011_03
Patent number
US07910606B2

Reaction notes

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