Tetrabutylammonium Fluoride → 3-Ethynylimidazo[1,2-b]pyridazine

HRID 1622532Notes

Reaction equation

HRID 1622532 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:11]2[N:12]=[CH:13][CH: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[N:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667355693-((Trimethylsilyl)ethynyl)imidazo[1,2-b]pyridazine

Product 1

HCID 468387603-Ethynylimidazo[1,2-b]pyridazineYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((trimethylsilyl)ethynyl)imidazo[1,2-b]pyridazine (28.46 g, 0.132 mol) in 200 mL of THF was added 145 mL (0.145 mol) 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 0-5% MeOH/DCM) to provide 17.84 g of product.

Workup

  1. concentrationconcentrated
  2. customthe crude product purified by silica gel flash chromatography (eluted with 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-4ad2af499e0c4653bd8469ff8ab00ec6
Source dataset
uspto-grants-2014_07
Patent number
US08778942B2

Reaction notes

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