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

HRID 1272120Notes

Reaction equation

HRID 1272120 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

A stirred 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 over 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 portions of 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 give 12.0 g (95.5%) of the desired product as a colourless 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 portions of 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-5f70bbfa6e9c47b9aaa64e74898d442e
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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