Ethanol → Ethyl 5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

HRID 2358165Notes

Reaction equation

HRID 2358165 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]([F:21])([F:20])[C:8]1[N:13]=[C:12]2[CH:14]=[C:15]([C:17]([OH:19])=[O:18])[NH:16][C:11]2=[CH:10][CH:9]=1.[CH2:22](O)[CH3:23]>>[F:21][C:7]([F:6])([F:20])[C:8]1[N:13]=[C:12]2[CH:14]=[C:15]([C:17]([O:19][CH2:22][CH3:23])=[O:18])[NH:16][C:11]2=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 573558695-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid

Product 1

HCID 66811603Ethyl 5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Procedure

1 ml (18.71 mmol) of concentrated sulfuric acid is added to a solution of 0.2 g (0.87 mmol) of 5-trifluoromethyl-pyrrolo[3,2-b]pyridine-2-carboxylic acid, obtained in step 19.2, in 10 ml of ethanol. The solution is refluxed for 20 hours and then cooled and concentrated under reduced pressure. The resulting residue is then taken up in 50 ml of dichloromethane and washed successively with 20 ml of saturated aqueous sodium hydrogen carbonate solution, 40 ml of water and 20 ml of saturated aqueous sodium chloride solution, dried over sodium sulfate and then concentrated under reduced pressure. 0.19 g of product is obtained, and is used without further purification in the following step.

Workup

  1. temperatureThe solution is refluxed for 20 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. washwashed successively with 20 ml of saturated aqueous sodium hydrogen carbonate solution, 40 ml of water and 20 ml of saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd3d76e2c89b4ef9818cbb747a2b8972
Source dataset
uspto-grants-2010_07
Patent number
US07763636B2

Reaction notes

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