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

HRID 588559Notes

Reaction equation

HRID 588559 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)acetamide

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 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, iso-hexanes/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, iso-hexanes/ethyl acetate 9:1 to 0:1)

Sources & evidence

ORD record
ord-1c90412283814f869eec97a998f7128f
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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