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

HRID 572985Notes

Reaction equation

HRID 572985 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-7691fb09671b4b11951e1fb3f4bc8217
Source dataset
uspto-grants-2015_05
Patent number
US09029533B2

Reaction notes

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