Tetrabutylammonium Fluoride → (3-Diethylamino-pyrrolidin-1-yl)-[5-(3-ethynyl-phenyl)-4-methyl-1H-pyrazol-3-yl]-methanone

HRID 1011923Notes

Reaction equation

HRID 1011923 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[CH:4]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[C:15]([CH3:16])=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[C:24][Si](C)(C)C)[CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH2:5]1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:29]([N:3]([CH2:1][CH3:2])[CH:4]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[C:15]([CH3:16])=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[CH:24])[CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH2:5]1)[CH3:30]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178463856HCID 178463856, compound

Product 1

HCID 178436202(3-Diethylamino-pyrrolidin-1-yl)-[5-(3-ethynyl-phenyl)-4-methyl-1H-pyrazol-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.101 g (0.24 mmol) of (3-diethylamino-pyrrolidin-1-yl)-[4-methyl-5-(3-trimethylsilanylethynyl-phenyl)-1H-pyrazol-3-yl]-methanone in 2.4 ml THF at 0° C. was treated with 0.26 ml (0.26 mmol) of 1M tetrabutylammonium fluoride in THF. The reaction was stirred at this temperature for 1.5 h and then partitioned between water/Et2O (3×). The organic phases were washed with water, dried (Na2SO4) and evaporated to give 0.084 g (quant) of the title compound as yellow foam. MS: 351.3 (MH+).

Workup

  1. custompartitioned between water/Et2O (3×)
  2. washThe organic phases were washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-5235d04941464d829bc1643e1e71e7d2
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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