Potassium Carbonate → HCID 57664740, compound

HRID 1717389Notes

Reaction equation

HRID 1717389 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]=3I)[CH:11]=2)=[O:6])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][C:32]#[CH:33]>CN(C=O)C.[Cu]I.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>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]=3[C:33]#[C:32][CH2:31][CH2:30][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:11]=2)=[O:6])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1233604-Phenyl-1-butyneHCID 57664776HCID 57664776, compound

Product 1

HCID 57664740HCID 57664740, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-iodophenyl}-1H-1,2,3-triazole-4-carboxamide (300 mg, 0.71 mmol) obtained in Example 382 in DMF (7.0 ml) were successively added potassium carbonate (200 mg), copper(I) iodide (15 mg), bis(triphenylphosphine)palladium(II) dichloride (25 mg) and but-3-yn-1-ylbenzene (110 mg), and the reaction mixture was stirred at room temperature overnight. Excess reagents and byproducts derived from the reagents were removed from the reaction mixture by adsorption onto silica gel column (ethyl acetate), and the eluate was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/4 to ethyl acetate) to give the title compound as a colorless powder (163 mg, 54%).

Workup

  1. customwere removed from the reaction mixture by adsorption onto silica gel column (ethyl acetate)
  2. customthe eluate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/4 to ethyl acetate)

Sources & evidence

ORD record
ord-a7c6e4da9d3b462f92961b229f089b79
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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