Dimethylformamide → HCID 21188055, compound

HRID 1383569Notes

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.CN(C)C=O.[CH2:27]([OH:30])[C:28]#[CH:29]>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:29]#[C:28][CH2:27][OH:30]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (200 mg, the compound of Example A1) in triethylamine (2 ml) and dimethylformamide (1 ml) at room temperature was added propargyl alcohol (0.2 ml), cuprous iodide (10 mg) and bis(triphenylphosphine)palladium(II) chloride (20 mg). The reaction mixture was heated at 70° C. for two hours. The reaction mixture was partitioned between ether (10 ml) and water (10 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 ether:dichloromethane (10:1) to provide the title compound as a pale yellow solid m.p. 237-9° C.

Workup

customThe reaction mixture was partitioned between ether (10 ml) and water (10 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 ether:dichloromethane (10:1)

Sources & evidence

ORD record: ord-0ab16ba369ef48218729708628323cfd
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255333B1

Reaction notes

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