Triethylamine → HCID 86684885, compound

HRID 238387Notes

Reaction equation

HRID 238387 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[CH:7]=[O:8].[C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=O)=[O:19])=[CH:14][CH:13]=1)#[CH:11].C([N:24](CC)CC)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.CN(C)C=O>[CH:7]([C:6]1[N:5]([CH3:9])[N:4]=[CH:3][C:2]=1[C:11]#[C:10][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:24])(=[O:21])=[O:19])=[CH:14][CH:13]=1)=[O:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 178534604-Iodo-1-methyl-1H-pyrazole-5-carbaldehydeHCID 86684886HCID 86684886, compound

Product 1

HCID 86684885HCID 86684885, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

A mixture of 4-iodo-1-methyl-1H-pyrazol-5-carbaldehyde (500 mg), 4-ethynylbenzenesulfonic acid (383 mg), copper(I) iodide (20 mg), bis(triphenylphosphine)palladium(II) dichloride (149 mg), triethylamine (600 μL) and dimethylformamide (10 mL) was stirred at 80° C. for 4 hours. Thereafter, the reaction solution was filtrated with Celite, and the filtrate was then washed with water. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=99:1 to 90:10), so as to obtain the title compound (580 mg) in the form of a light yellow solid.

Workup

  1. filtrationThereafter, the reaction solution was filtrated with Celite
  2. washthe filtrate was then washed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationwas then concentrated under a reduced pressure
  5. customThe residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=99:1 to 90:10)

Sources & evidence

ORD record
ord-895ceaa5b5be4090ad28cadeb13629e0
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

Loading…