Potassium Fluoride → HCID 178437211, compound

HRID 1843658

Reaction equation

HRID 1843658 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:14]([C:15]#[C:16][Si](C)(C)C)=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F-].[K+]>CO>[C:15]([C:14]1[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[N:11][NH:12][CH:13]=1)#[CH:16]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 1785041883-(3-nitrophenyl)-4-[(trimethylsilyl)ethynyl]-1H-pyrazole

Product 1

HCID 178437211HCID 178437211, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

300 mg (1.05 mmol) of 3-(3-nitrophenyl)-4-[(trimethylsilyl)ethynyl]-1H-pyrazole were suspended in 60 ml of methanol and 120 mg (2.1 mmol) of potassium fluoride were added and the mixture stirred at room temperature overnight. After this time the solvent was removed under reduced pressure and the residue taken up with dichloromethane and washed with water. The organic layer was then dried over sodium sulphate and evaporated. The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 9/1), giving 150 mg (67%) of the title compound.

Workup

  1. customAfter this time the solvent was removed under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. customevaporated
  5. customThe crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 9/1)

Sources & evidence

ORD record
ord-9c6642fca7364a53afa1170ce7712230
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Linked notes

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