Trifluoroacetic acid → Pyrrolo[3,2-c]pyridin-1-yl-acetic acid

HRID 651627Notes

Reaction equation

HRID 651627 reaction equation
C([O:5][C:6](=[O:17])[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[CH:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:8]1([CH2:7][C:6]([OH:17])=[O:5])[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54447290Pyrrolo[3,2-c]pyridin-1-yl-acetic acid tert-butyl ester

Product 1

HCID 18176302Pyrrolo[3,2-c]pyridin-1-yl-acetic acidYield 150.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pyrrolo[3,2-c]pyridin-1-yl-acetic acid tert-butyl ester (0.44 g, 1.89 mmol) in CH2Cl2 (10 mL) at 0° C. is added trifluoroacetic acid (1 mL). After 15 minutes, the solution is allowed to warm to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and then azeotroped with toluene to give 0.5 g of the title compound as a residue (wet with excess TFA) which is used as is in the subsequent step

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-70f83433f2d34839bb2a66a629b56a34
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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