Sodium methanesulfinate → 3-(6-Methanesulfonyl-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

HRID 1466874

Reaktionsgleichung

Reaktionsgleichung von HRID 1466874
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16](Br)=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[CH3:23][S:24]([O-:26])=[O:25].[Na+]>CN1C(=O)CCC1.[Cu]I>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([S:24]([CH3:23])(=[O:26])=[O:25])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1

Komponenten

5

Edukt 2

HCID 2733271Sodium methanesulfinateHCID 667653623-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

Produkt 1

HCID 667650383-(6-Methanesulfonyl-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

3-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.113 g, 0.3 mmol), sodium methanesulfinate (0.138 g, 1.35 mmol), and copper(I) iodide (0.257 g, 1.35 mmol) were combined in NMP (3 mL) in a sealed reaction vessel and stirred at 140° C. for overnight. The resulting mixture was cooled to room temperature, and subjected to standard aqueous workup. The crude residue was purified by silica gel chromatography (10-100% EtOAc in hexanes) to afford the title compound.

Aufarbeitung

  1. temperatureThe resulting mixture was cooled to room temperature
  2. customThe crude residue was purified by silica gel chromatography (10-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-900c4c1a9b034bad9f4f54da8762a7ef
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000025B2

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