Triethylamine → N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

HRID 1615703Notes

Reaction equation

HRID 1615703 reaction equation
I[C:2]1[CH:3]=[N:4][NH:5][C:6]=1[NH:7][C:8](=[O:10])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:37]1([C:43]#[CH:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>[Pd].C(O)C.[Cu]I>[C:37]1([C:43]#[C:44][C:2]2[CH:3]=[N:4][NH:5][C:6]=2[NH:7][C:8](=[O:10])[CH3:9])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 86717260N-(4-iodo-1H-pyrazol-5-yl)acetamide

Product 1

HCID 86717261N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamideYield 65.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolvent

Procedure

Nitrogen was bubbled through a suspension of N-(4-iodo-1H-pyrazol-5-yl)acetamide (30 g, 120 mmol), 10% palladium on carbon (50% water, 7.4 g, 3 mmol), copper(I) iodide (1.14 g, 6 mmol), triphenylphosphine (6.3 g, 24 mmol) and triethylamine (50 mL, 360 mmol) in ethanol (600 mL) for 20 min. Phenyl acetylene (18.3 g, 179 mmol) was added and nitrogen bubbled through the mixture for a further 25 min. The reaction mixture was then heated and stirred under reflux conditions in an atmosphere of nitrogen for 3 d and cooled to room temperature. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 9:1 to 0:1) yielding the title compound as a solid (17.6 g).

Workup

  1. customnitrogen bubbled through the mixture for a further 25 min
  2. temperatureThe reaction mixture was then heated
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 9:1 to 0:1)

Sources & evidence

ORD record
ord-fd4b46c53f5147b5ba9ebd84a4e3d8ba
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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