Tetrabutylammonium Fluoride → 3-Ethynyl-imidazo[1,2-A]pyrazine

HRID 1622501Notes

Reaction equation

HRID 1622501 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:11]2[CH:12]=[CH:13][N:14]=[CH:15][C:10]2=[N:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:6]([C:7]1[N:11]2[CH:12]=[CH:13][N:14]=[CH:15][C:10]2=[N:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667356023-((Trimethylsilyl)ethynyl)imidazo[1,2-a]pyrazine

Product 1

HCID 722072723-Ethynyl-imidazo[1,2-A]pyrazineYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((Trimethylsilyl)ethynyl)imidazo[1,2-a]pyrazine (0.15 g, 0.7 mmol) in 3.5 mL of THF was added 1.05 mL (1.05 mmol) of tetrabutylammonium fluoride (1.0M in THF) at ambient temperature. The solution was stirred for 15 min, concentrated, and the crude product purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes) to provide 0.078 g of product.

Workup

  1. concentrationconcentrated
  2. customthe crude product purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-998c025852a7439490243a2426c70ae5
Source dataset
uspto-grants-2014_07
Patent number
US08778942B2

Reaction notes

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