Tetrabutylammonium Fluoride Trihydrate → HCID 46219698, compound

HRID 1924510Notes

Reaction equation

HRID 1924510 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10](=[O:13])[C:9]([C:14]3[N:15]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][Si](C)(C)C)[CH:20]=4)[N:16]=[CH:17][CH:18]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-]>C1COCC1>[C:25]([C:21]1[CH:20]=[C:19]([N:15]2[C:14]([C:9]3[C:10](=[O:13])[CH:11]=[CH:12][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)=[CH:18][CH:17]=[N:16]2)[CH:24]=[CH:23][CH:22]=1)#[CH:26]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 59369982HCID 59369982, compound

Product 1

HCID 46219698HCID 46219698, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-phenyl-3-[2-(3-trimethylsilanylethynyl-phenyl)-2H-pyrazol-3-yl]-1H-pyridazin-4-one (example 31, 50 mg, 0.12 mmol) is dissolved in THF (2 ml). Tetrabutylammoniumfluoride trihydrate (77 mg, 0.24 mmol) is added at 0° C. and the reaction mixture is allowed to warm up to ambient temperature within 15 minutes. Stirring is continued for another 2 hours. The reaction mixture is quenched with water and extracted with ethyl acetate. The solvent is removed and the obtained crude product is triturated with diethyl ether. The solid material is filtrated and dried to obtain 39 mg (94% yield) of the product.

Workup

  1. customThe reaction mixture is quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe solvent is removed
  4. customthe obtained crude product
  5. customis triturated with diethyl ether
  6. filtrationThe solid material is filtrated
  7. customdried

Sources & evidence

ORD record
ord-9d3d78a4664e4a298c9c4d538058fca8
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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