Trimethylsilylacetylene → 1-phenyl-5-[(trimethylsilyl)ethynyl]-1H-pyrazole

HRID 1747824Notes

Reaction equation

HRID 1747824 reaction equation
I[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][CH:3]=1.[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14]>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>[C:7]1([N:6]2[C:2]([C:14]#[C:13][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:3][CH:4]=[N:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 149720775-Iodo-1-phenyl-1H-pyrazole

Product 1

HCID 895862591-phenyl-5-[(trimethylsilyl)ethynyl]-1H-pyrazoleYield 86.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-iodo-1-phenyl-1H-pyrazole (2.00 g) (J. Org. Chem. 2008, 73, 1, 177-183) in triethylamine (40.0 mL) were added ethynyl(trimethyl)silane (0.80 g), CuT (0.141 g) and PdCl2(PPh3)2 (0.260 g) under an argon atmosphere, and the mixture was stirred at 70° C. for 10 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane) to give the title compound (1.54 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-d193ca8d67d64c58929a5537ef749839
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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