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

HRID 1097265Notes

Reaction equation

HRID 1097265 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-c497cfbb5e4140b98bb86e51e764b860
Source dataset
uspto-grants-2012_03
Patent number
US08143248B2

Reaction notes

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