Toluene → 1H-Indole-2,4-dicarboxylic acid 4-methyl ester

HRID 460007Notes

Reaction equation

HRID 460007 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[C:8]([C:14]([O:16]C(C)(C)C)=[O:15])[NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].C1(C)C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[C:8]([C:14]([OH:16])=[O:15])[NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 1140TolueneHCID 688587391H-Indole-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester

Product 1

HCID 695071401H-Indole-2,4-dicarboxylic acid 4-methyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3.8 g 1H-Indole-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester were dissolved in 100 ml TFA. After 1 h at RT 150 ml toluene were added and the solvents were removed under reduced pressure. The residue was lyophilised after addition of water and acetonitrile. Yield: 2 g.

Workup

  1. customthe solvents were removed under reduced pressure
  2. additionafter addition of water and acetonitrile

Sources & evidence

ORD record
ord-a25b45ed7b9145c498fd80725359f84a
Source dataset
uspto-grants-2007_03
Patent number
US07196103B2

Reaction notes

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