Dimethylformamide → HCID 57429654, compound

HRID 888999Notes

Reaction equation

HRID 888999 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]#[CH:13])[CH:10]=1)=[O:5])[CH3:2].I[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.CN(C=O)C>O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]#[C:13][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 122074-IodotolueneHCID 57429655HCID 57429655, compound

Product 1

HCID 57429654HCID 57429654, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-prop-2-ynyl-1H-pyrazole-4-carboxylic acid ethyl ester obtained as given in example B1 (0.200 g, 1.1 mmol), 4-iodo toluene (0.254 g, 1.1 mol), copper iodide (0.021 g, 0.11 mmol), dichlorobis (triphenylphosphine)-palladium (II) (39 mg, 0.06 mmol), triethylamine (2 ml), DMF (2 ml) was degassed for 10 min. and stirred for 20 hrs at 25-25° C. Reaction mixture was diluted with water (10 ml) and extracted with ethyl acetate. Organic layer was washed with brine solution and dried over Na2SO4. The solvent was evaporated and crude product was purified by column chromatography (Ethyl acetate:hexane-12:78) to obtain pure 1-(3-p-tolyl-prop-2-ynyl)-1H-pyrazole-4-carboxylic acid ethyl ester compound (0.226 g, 75%).

Workup

  1. customobtained
  2. customwas degassed for 10 min.
  3. customReaction mixture
  4. extractionextracted with ethyl acetate
  5. washOrganic layer was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. customcrude product was purified by column chromatography (Ethyl acetate:hexane-12:78)

Sources & evidence

ORD record
ord-63333bf9e12e402e9fe8d2e380df2db3
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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