Pyridine → 2-chloro-4-{[1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid methyl ester

HRID 2235078

Reaktionsgleichung

Reaktionsgleichung von HRID 2235078
[Cl:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14](=[O:34])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:32]=[C:31]3[C:27]([CH2:28][CH2:29][NH:30]3)=[CH:26][CH:25]=2)=[O:23])=[CH:17][C:16]=1[Cl:33].N1C=CC=CC=1>ClCCl>[CH3:12][O:13][C:14](=[O:34])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:32]=[C:31]3[C:27]([CH2:28][CH2:29][N:30]3[S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:10])=[O:9])=[CH:26][CH:25]=2)=[O:23])=[CH:17][C:16]=1[Cl:33]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 179093-Chlorobenzenesulphonyl chlorideHCID 686984452-chloro-4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester

Produkt 1

HCID 686961202-chloro-4-{[1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Chlorobenzenesulphonyl chloride (71 mg, 0.3 mmol, 1.1 equiv.) was added to a mixture of crude 2-chloro-4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester (100 mg, 0.3 mmol, 1 equiv.) and pyridine (0.2 mL, 2.4 mmol, 8 equiv.) in dichloromethane (2 ml) and the mixture was stirred at room temperature for 16 hours. The solvent was removed under a stream of N2 and the residue purified by column chromatography (SiO2, dichloromethane). The fractions were combined to afford crude 2-chloro-4-{[1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid methyl ester, 101 mg. This material was taken onto the next step without further purification. LC @215 nm; Rt 2.52: 84%, m/z (ES+): 505 (M+H+.).

Aufarbeitung

  1. customThe solvent was removed under a stream of N2
  2. customthe residue purified by column chromatography (SiO2, dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a6ca3900af214f7893f1f298564e0097
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713996B2

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