Sodium ethoxide → 4-Azaindole

HRID 392129

Reaction equation

HRID 392129 reaction equation
FC(F)(F)C([NH:5][C:6]1[C:7]([C:12]#[C:13][Si](C)(C)C)=[N:8][CH:9]=[CH:10][CH:11]=1)=O.[O-]CC.[Na+]>C(O)C>[NH:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:12]=[CH:13]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 121468532,2,2-trifluoro-N-(2-trimethylsilanylethynylpyridin-3-yl)acetamide

Product 1

HCID 92264-Azaindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,2,2-trifluoro-N-(2-trimethylsilanylethynylpyridin-3-yl)acetamide (1.0 eq) and sodium ethoxide (5 eq.) in ethanol is heated at reflux temperature for 10 h, cooled and concentrated in vacuo. The resultant residue is purified by preparative reverse phase HPLC to give the title 4-azaindole.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 10 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-2930650ca1d249b885405ad26de4d25a
Source dataset
uspto-grants-2004_10
Patent number
US06800640B2

Linked notes

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