Water → 6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid

HRID 514266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514266
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])[NH:8]2)=[CH:4][C:3]=1[C:29]([O:31]CC)=[O:30].B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:16])([F:15])[F:17])[NH:8]2)=[CH:4][C:3]=1[C:29]([OH:31])=[O:30]

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 58247983Ethyl 6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate

Produkt 1

HCID 867139846-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acidAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Ethyl 6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate (2.90 g, 5.0 mmol, 85% pure) was dissolved in 5 ml of dichloromethane and a solution of boron tribromide in dichloromethane (27.5 ml, 27.5 mmol) was added dropwise at −10° C. The reaction mixture was stirred at −10° C. for 1 h and then at room temperature for 2 h. Water was added and the precipitated solid was filtered off with suction and dried. 1.85 g (79% of theory) of 6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid were obtained.

Aufarbeitung

  1. waitat room temperature for 2 h
  2. filtrationthe precipitated solid was filtered off with suction
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1845da64d6b0495583bfd9c4128e84ae
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107411B2

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