Trifluoroacetic acid → 2-((1H-indol-5-yl)amino)-4-phenylbenzoic acid

HRID 2191714Notes

Reaction equation

HRID 2191714 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[CH:37]=[C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:35]=[CH:34][C:26]=3[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=O)(C)(C)C>>[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[CH:37]=[C:36]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:35]=[CH:34][C:26]=3[C:27]([OH:29])=[O:28])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68959368tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenylbenzoate

Product 1

HCID 576679072-((1H-indol-5-yl)amino)-4-phenylbenzoic acid

Procedure

Trifluoroacetic acid 5 mL solution of the obtained tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenylbenzoate was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 50-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((1H-indol-5-yl)amino)-4-phenylbenzoic acid 8 mg of yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3db7935c9af746f69270114ff83e308c
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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