Trifluoroacetic acid → HCID 73013608, compound

HRID 1272108Notes

Reaction equation

HRID 1272108 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:16](C(OC(C)(C)C)=O)[C:9]2=[N:10][C:11]([Cl:15])=[C:12]([CH3:14])[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:16][C:9]2=[N:10][C:11]([Cl:15])=[C:12]([CH3:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73013562HCID 73013562, compound

Product 1

HCID 73013608HCID 73013608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.53 g (1.56 mmol) 6-chloro-5-methyl-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 8 mL dichloromethane was cooled to 0° C., 1.44 mL (2.14 g, 18.8 mmol) trifluoroacetic acid was added and the cooling bath removed. After 2 h the volatile components were removed and the residue was poured into saturated 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 off-white solid (91.1%) was used without further purification.

Workup

  1. customthe cooling bath removed
  2. customAfter 2 h the volatile components were removed
  3. additionthe residue was poured into saturated 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 off-white solid (91.1%) was used without further purification

Sources & evidence

ORD record
ord-fb9078f740374a3d9be860ce5fc8e444
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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