Methyl iodide → [3-(6-Chloro-1,2-dimethyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

HRID 1466760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466760
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:12][C:13]3[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=3)=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1.I[CH3:24]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:12][C:13]3[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=3)=[C:7]([CH3:11])[N:8]2[CH3:24])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 66765068[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Produkt 1

HCID 56840628[3-(6-Chloro-1,2-dimethyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid (0.062 g, 0.19 mmol) was dissolved in DMF (3 mL) and cooled to −10° C. and then sodium bis(trimethyl)amide solution (0.420 mL, 0.42 mmol, 1.0M solution) was added. The reaction was stirred for 1 hour then iodomethane (13 μL, 0.21 mmol) was added in one portion. Standard aqueous workup and purification by preparatory HPLC provided the title compound.

Aufarbeitung

  1. customStandard aqueous workup and purification by preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-43ed5be543dc47f39d5f7eda6815f51d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000025B2

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