Benzenesulfonyl chloride, 3,4-dichloro- → methyl N-(3,4-dichlorophenylsulphonyl)-5-benzyloxyindole-2-carboxylate

HRID 1582648Notes

Reaction equation

HRID 1582648 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([O:22][CH3:23])=[O:21])=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:24][C:25]1[CH:26]=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:28]=[CH:29][C:30]=1[Cl:31]>CN(C=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([S:32]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([O:10][CH2:3][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)=[CH:19][CH:18]=3)[CH:14]=[C:15]2[C:20]([O:22][CH3:23])=[O:21])(=[O:33])=[O:34])[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

5

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 24758Sodium hydrideHCID 4777669Methyl 5-(Benzyloxy)-1H-indole-2-carboxylate

Product 1

HCID 22718745methyl N-(3,4-dichlorophenylsulphonyl)-5-benzyloxyindole-2-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium Hydride (60% dispersion, 444 mg) was added to a stirred solution of methyl 5-benzyloxyindole-2-carboxylate (2.08 g) in DMF (50 ml) at room temperature. After 1 hour, 3,4-dichlorobenzenesulphonyl chloride (2.72 g) was added. Stirring was continued for 2 hours after which the reaction mixture was partitioned between water and ethyl acetate. Combined organic extracts were dried and concentrated in vacuo and the residue purified by column chromatography using isohexane-20% ethyl acetate as eluent to give the desired product as a white solid (2.02 g, 56%). NMR: δ3.85 (s, 3H), 5.1 (s, 2H), 7.2 (m, 1H), 7.4 (m, 7H), 7.9 (s, 2H), 8.0 (d, 1H), 8.2 (s, 1H); m/z 489.8 (MH+).

Workup

  1. waitwas continued for 2 hours
  2. customafter which the reaction mixture was partitioned between water and ethyl acetate
  3. customCombined organic extracts were dried
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-51a38b9d6eaa4024a767e21764dc1cc1
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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