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

HRID 1640462Notes

Reaction equation

HRID 1640462 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-312dbc2b50394c8689fd4e9c2f0fefd5
Source dataset
uspto-grants-2012_02
Patent number
US08114874B2

Reaction notes

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