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

HRID 1582648노트

반응식

HRID 1582648 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-51a38b9d6eaa4024a767e21764dc1cc1
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737435B1

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