Trifluoroacetic acid → Ethyl 6-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 11910Notes

Reaction equation

HRID 11910 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:15](C(OC(C)(C)C)=O)[C:9]2=[N:10][C:11]([Br:14])=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH2:2]([O:3][C:4]([C:6]1[NH:15][C:9]2=[N:10][C:11]([Br:14])=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57360935HCID 57360935, compound

Product 1

HCID 46839969Ethyl 6-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 18.4 g (0.05 mol) 6-bromo-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 165 ml dichloromethane was cooled to 0 deg C. and then 38.0 ml trifluoroacetic acid was added within 5 min. The cooling bath was removed and after 2 h at room temperature the reaction mixture was poured into 500 ml saturated aqueous sodium bicarbonate solution. The organic layer was extracted three times with 150 ml dichloromethane. The combined organic phases were washed with 200 ml brine, dried over magnesium sulfate and filtered. The solvent was evaporated and the residue was dried under high vacuum to afford 12.0 g (95.5%) of the desired product as a colorless solid.

Workup

  1. customThe cooling bath was removed and after 2 h at room temperature the reaction mixture
  2. additionwas poured into 500 ml saturated aqueous sodium bicarbonate solution
  3. extractionThe organic layer was extracted three times with 150 ml dichloromethane
  4. washThe combined organic phases were washed with 200 ml brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-b0b2eccfe6484bd781c52236855a5bd0
Source dataset
uspto-grants-2006_08
Patent number
US07098337B2

Reaction notes

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