Tetrabutylammonium Fluoride → N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide

HRID 1916743Notes

Reaction equation

HRID 1916743 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][C:20]1[C:21]([NH:32][C:33](=[O:40])[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[N:22][CH:23]=[C:24]([C:26]#[C:27][Si](C)(C)C)[CH:25]=1>C1COCC1>[C:26]([C:24]1[CH:25]=[C:20]([CH3:19])[C:21]([NH:32][C:33](=[O:40])[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[N:22][CH:23]=1)#[CH:27]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67363112N-(3-methyl-5-trimethylsilanylethynyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide

Product 1

HCID 85969661N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 132 mg (0.48 mmol) TBAF are added to a solution of 150 mg (0.48 mmol) N-(3-methyl-5-trimethylsilanylethynyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide in 10 mL THF and the reaction mixture is stirred overnight at RT. The mixture is evaporated down i. vac., the residue is taken up in EtOAc, the organic phase is washed with water and saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the desired product is obtained.

Workup

  1. customThe mixture is evaporated down i
  2. washthe organic phase is washed with water and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis obtained

Sources & evidence

ORD record
ord-b791fe6d7d1d45459ab8bc5cbc24bfb6
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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