Sulfuric Acid → 5-Trifluoromethyl-1H-pyrrolo[2,3-b]pyridine 2-ethyl carboxylate

HRID 1019528Notes

Reaction equation

HRID 1019528 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][C:6]2=[N:7][CH:8]=1.S(=O)(=O)(O)O>C(O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.[CH3:11][CH2:10][C:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 547588435-(trifluoromethyl)-1H-pyrrolo(2,3-b)pyridine-2-carboxylic acid

Product 1

HCID 866390565-Trifluoromethyl-1H-pyrrolo[2,3-b]pyridine 2-ethyl carboxylateYield 172.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Put 0.3 g (1.3 mmol) of 5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (Angew Chem Int Ed 2004, 43(34), 4526-4528) and 50 mL of ethanol in a 100-mL flask equipped with a magnetic stirrer. Add, to this solution, 0.5 mL of concentrated sulfuric acid. The reaction mixture is then refluxed for 18 hours. The cooled solution is concentrated to dryness at reduced pressure. The residue is taken up in dichloromethane (100 mL), the organic phase is washed successively with a normal aqueous solution of sodium hydroxide (30 mL), with water (20 mL) and then with a saturated aqueous solution of sodium chloride. It is dried over sodium sulfate and then concentrated at reduced pressure. 0.29 g (1.12 mmol) of the expected product is isolated in the form of a yellow powder.

Workup

  1. temperatureThe reaction mixture is then refluxed for 18 hours
  2. concentrationThe cooled solution is concentrated to dryness at reduced pressure
  3. washthe organic phase is washed successively with a normal aqueous solution of sodium hydroxide (30 mL), with water (20 mL)
  4. dry with materialIt is dried over sodium sulfate
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-f7328e10a6204f3792ace343303e9e9a
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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