Sodium ethoxide → 4-Azaindole

HRID 1593499Notes

Reaction equation

HRID 1593499 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-trimethylsilan-ylethynylpyridin-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-09717a68dac346a48f51859a0b80a69b
Source dataset
uspto-grants-2007_11
Patent number
US07297705B2

Reaction notes

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