Tetrabutylammonium Fluoride Trihydrate → HCID 59453402, compound

HRID 714555Notes

Reaction equation

HRID 714555 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([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: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:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=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 59453399HCID 59453399, compound

Product 1

HCID 59453402HCID 59453402, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-Pyridin-4-yl-3-[2-(3-trimethylsilanylethynyl-phenyl)-2H-pyrazol-3-yl]-1H-pyridazin-4-one (example 98, 33 mg, 0.08 mmol) is dissolved in THF (1 ml). Tetrabutylammoniumfluoride trihydrate (51 mg, 0.16 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 1 hour. The reaction mixture is quenched with water and extracted with ethyl acetate. The solvent is removed and the obtained crude product is purified by chromatography on silica gel using EtOAC/MeOH gradient to obtain 22 mg (81% yield) of the product. MS: M=340.1 (M+H)+

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 purified by chromatography on silica gel using EtOAC/MeOH gradient

Sources & evidence

ORD record
ord-00ef4e9ca7954bcda7d5308d8897975d
Source dataset
uspto-grants-2015_11
Patent number
US09187455B2

Reaction notes

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