Phenylacetylene → HCID 18677777, compound

HRID 1634279Notes

Reaction equation

HRID 1634279 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=[CH:14][C:13]([C:23]([F:26])([F:25])[F:24])=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:27]1([C:33]#[CH:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:34]#[C:33][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:18][CH:17]=3)=[CH:14][C:13]([C:23]([F:26])([F:25])[F:24])=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 15340994HCID 15340994, compound

Product 1

HCID 18677777HCID 18677777, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-[4-(methylsulfonyl)phenyl]-5-(4-bromophenyl)-3-trifluoromethyl-1H-pyrazole (445 mg; 1 mmol) and phenylacetylene (102 mg; 1 mmol) in pyrrolidine (2 mL) was added tetrakis(triphenylphosphine)palladium (35 mg) under a nitrogen atmosphere, and the mixture was heated at 80° C. for 1 hour. After cooling, the volatiles were removed by evaporation. The residue was purified by flash chromatography (SiO2) eluting with ethyl acetate/hexane (1:3) to give the title compound (0.4 g, 86% yield).

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed by evaporation
  3. customThe residue was purified by flash chromatography (SiO2)
  4. washeluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-3ee9a0065c434af499016a88b973911d
Source dataset
uspto-grants-2003_01
Patent number
US06506779B1

Reaction notes

Loading…