Trifluoroacetic acid → HCID 73013607, compound

HRID 1272100Notes

Reaction equation

HRID 1272100 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:18](C(OC(C)(C)C)=O)[C:9]2=[N:10][C:11]([Cl:17])=[C:12]([O:14][CH2:15][CH3:16])[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:18][C:9]2=[N:10][C:11]([Cl:17])=[C:12]([O:14][CH2:15][CH3:16])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73013559HCID 73013559, compound

Product 1

HCID 73013607HCID 73013607, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (2.71 mmol) 6-chloro-5-ethoxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 20 mL dichloromethane was cooled to 0° C., 10 mL (14.9 g, 0.13 mol) trifluoroacetic acid was added and then the cooling bath was removed. After 1 h the volatile components were removed and the residue was poured into 10% aqueous sodium bicarbonate solution and extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The resulting white solid (100%) was used without further purification.

Workup

  1. customthe cooling bath was removed
  2. customAfter 1 h the volatile components were removed
  3. additionthe residue was poured into 10% aqueous sodium bicarbonate solution
  4. extractionextracted twice with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting white solid (100%) was used without further purification

Sources & evidence

ORD record
ord-c5e999d66af44e1bae54ff058c5ff7b4
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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