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

HRID 1582648ノート

反応式

HRID 1582648 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-51a38b9d6eaa4024a767e21764dc1cc1
出典データセット
uspto-grants-2004_05
特許番号
US06737435B1

反応ノート

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