Methyl iodide → 5-iodo-1-methyl-1H-indole

HRID 1258422

Reaktionsgleichung

Reaktionsgleichung von HRID 1258422
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CI.[C:13]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:13])[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27823135-Iodo-1H-indole

Produkt 1

HCID 113228355-iodo-1-methyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Iodoindole (4.8 g, 20 mmol) was stirred in dry DMF (20 ml) containing MeI (8.5 g, 60 mmol) and K2CO3 (13.8 g, 100 mmol) for overnight at 55° C. The reaction mixture was diluted with EtOAc and passed through celite plug. The illiterate was evaporated to dryness and then oil was further purified by small flash column, Yield (90%). 1H NMR (300 MHz, CDCl3) δ: 3.75 (s, 3H, NMe), 6.39 (d, J=3.0, 1H), 6.98 (d, J=3.0, 1H), 7.07 (d, J=9.0, 1H), 7.44 (dd, J1=9.0, J2=1.2, 1H), 7.93 (d, J=1.2, 1H).

Aufarbeitung

  1. customThe illiterate was evaporated to dryness
  2. customoil was further purified by small flash column
  3. customYield (90%)

Quellen und Nachweise

ORD-Eintrag
ord-70e45e5efd8642a08989a8c163b48859
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466163B2

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