Water → HCID 21188071, compound

HRID 1383576Notes

Reaction equation

[C:1]([C:3]1[C:7](I)=[C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[N:5]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:4]=1)#[N:2].[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28].O.C(OCC)C>C(N(CC)CC)C.CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]([C:3]1[C:7]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])=[C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[N:5]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:4]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-iodo-5-(N-pyrrolyl)pyrazole (0.55 g) in triethylamine (1 ml) and dimethylformamide (10 ml) was added trimethylsilylacetylene (1 ml), cuprous iodide (15 mg) and bis(triphenylphosphine)palladium (II) chloride (30 mg). The reaction mixture was heated at 70° C. for 24 hours, and then poured into water (100 ml) and diethyl ether (100 ml). The organic layer was dried over MgSO4 and the solvent was evaporated. The crude product was purified by chromatography on silica gel (50 g), eluting with dichloromethane: hexane (1:1), giving the title compound as a pale brown solid.

Workup

dry with materialThe organic layer was dried over MgSO4
customthe solvent was evaporated
customThe crude product was purified by chromatography on silica gel (50 g)
washeluting with dichloromethane: hexane (1:1)

Sources & evidence

ORD record: ord-f842778bfc3f48a99d3a39aff34a8110
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255333B1

Reaction notes

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