methyl N-(3,4-dichlorophenylsulphonyl)-5-benzyloxyindole-2-carboxylate → Methyl n-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylate

HRID 1582649Notes

Reaction equation

HRID 1582649 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21]CC4C=CC=CC=4)=[CH:18][CH:19]=3)[CH:14]=[C:13]2[C:29]([O:31][CH3:32])=[O:30])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=3)[CH:14]=[C:13]2[C:29]([O:31][CH3:32])=[O:30])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 22718745methyl N-(3,4-dichlorophenylsulphonyl)-5-benzyloxyindole-2-carboxylate

Product 1

HCID 22718735Methyl n-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylateYield 16.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5% palladium on carbon in ethyl acetate (450 ml) and methyl N-(3,4-dichlorophenylsulphonyl)-5-benzyloxyindole-2-carboxylate(2.01 g) was stirred at 60° c under hydrogen at atmospheric pressure for 48 hours. The catalyst was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography using 20%ethyl acetate/isohexane as eluent to give the desired product as a gum (270 mg,16%). NMR: δ 3.85(s, 31H), 7.0 (m, 2H), 7.35 (s, 1H), 7.9 (m, 3H), 8.1 (s, 1H), 9.6 (s, 1H); m/z 401.9 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9a8671b25b3246ffb4e2ece8b42eed5a
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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