3-Methylbut-1-yne → HCID 21188054, compound

HRID 1383568Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1I.[CH3:22][CH:23]([CH3:26])[C:24]#[CH:25]>C(N(CC)CC)C.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>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:25]#[C:24][CH:23]([CH3:26])[CH3:22]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (447 mg, the compound of Example A1) in triethylamine (10 ml) at room temperature was added 3-methylbut-1-yne (0.5 ml), cuprous iodide (15 mg) and bis(triphenylphosphine)palladium(II) chloride (30 mg). The reaction mixture was heated at 70° C. for two hours. The reaction mixture was partitioned between ether (100 ml) and water (100 ml). The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with dichloromethane: hexane (1:1) to provide the title compound as a pale yellow solid m.p. 210-2° C.

Workup

customThe reaction mixture was partitioned between ether (100 ml) and water (100 ml)
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by column chromatography on silica gel
washeluted with dichloromethane: hexane (1:1)

Sources & evidence

ORD record: ord-aefeaf5d9a9a4307823743ad86285c1c
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255333B1

Reaction notes

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