Benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylate → 1-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylic acid

HRID 1604678Notes

Reaction equation

HRID 1604678 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([C:30]([O:32]CC5C=CC=CC=5)=[O:31])=[CH:22]4)=[O:20])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([C:30]([OH:32])=[O:31])=[CH:22]4)=[O:20])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 19603790Benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylate

Product 1

HCID 196037211-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylic acidYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylate (107 mg) in tetrahydrofuran (4 ml) was hydrogenated over 10% Pd--C (22 mg) at room temperature under atmospheric pressure. After removal of the catalyst by filtration, the filtrate was concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-carboxylic acid (74.5 mg).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e3013588b414ad9992287cf0c9ea83f
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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