Sodium ethoxide → 4-Azaindole

HRID 2080015Notes

Reaction equation

HRID 2080015 reaction equation
C(OC(=O)[NH:5][C:6]1[C:7]([C:12]#[C:13][Si](C)(C)C)=[N:8][CH:9]=[CH:10][CH:11]=1)C.[O-]CC.[Na+]>C(O)C.[Cl-].[Na+].O>[NH:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:12]=[CH:13]1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 58875356(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester

Product 1

HCID 92264-AzaindoleYield 63.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester described in Preparation Example S-3 (0.42 g, 1.6 mmol) was dissolved in ethanol (8 mL), sodium ethoxide (204 mg, 3 mmol) was added thereto, followed by stirring for 1 hour under reflux. After the reaction was completed, the reaction mixture was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then evaporated, the resulting solid was washed with solvent (diethylether:hexane=1:2), and the title compound (0.12 g, 1 mmol, 63.5%) was obtained.

Workup

  1. temperatureunder reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. washthe resulting solid was washed with solvent (diethylether:hexane=1:2)

Sources & evidence

ORD record
ord-216d4aea7c184db1a07535b90590f960
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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