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

HRID 2063289Notes

Reaction equation

HRID 2063289 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 sulphuric acid is added to a solution of 0.2 g (0.87 mmol) of 5-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid, obtained in step 23.2, in 10 ml of ethanol. The solution is stirred at reflux for 20 hours and then cooled and concentrated under reduced pressure. The resultant residue is subsequently taken up with 50 ml of dichloromethane and then washed successively with 20 ml of a saturated aqueous solution of sodium hydrogen carbonate, 40 ml of water and 20 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulphate and then concentrated under reduced pressure. 0.19 g of product is obtained, which product is used as it is in the subsequent step.

Workup

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

Sources & evidence

ORD record
ord-0e5183b9461b4b9f90bd3a485694ae56
Source dataset
uspto-grants-2012_10
Patent number
US08288376B2

Reaction notes

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