Sodium ethoxide → 4-Azaindole

HRID 731588Notes

Reaction equation

HRID 731588 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-15f7cf4f5e854ea4940f8df56fe1e545
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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