Dimethylformamide → HCID 86684880, compound

HRID 238382Notes

Reaction equation

HRID 238382 reaction equation
CN(C)C=O.I[C:7]1[CH:8]=[N:9][N:10]([CH3:22])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25].C(N(CC)CC)C>C(OCC)(=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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:22][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[C:7]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[CH:8]=[N:9]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86684878HCID 86684878, compound

Product 1

HCID 86684880HCID 86684880, compoundYield 83.8%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

Under a nitrogen atmosphere, copper(I) iodide (7 mg), bis(triphenylphosphine)palladium(II) dichloride (90 mg) and triphenylphosphine (34 mg) were added to a dimethylformamide (45 mL) solution that contained 4-iodo-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazole (4.51 g), trimethylsilylacetylene (2.26 g) and triethylamine (3.57 mL), and the obtained solution was then stirred at 75° C. for 4 hours. Thereafter, the reaction solution was diluted with ethyl acetate, and was then washed with water and a saturated saline. 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 60N, hexane:ethyl acetate=85:15 to 70:30), so as to obtain the title compound (3.46 g).

Workup

  1. washwas then washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated under a reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=85:15 to 70:30)

Sources & evidence

ORD record
ord-d1e830a8122745c0a654bc42cfc8452a
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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