Methyl iodide → ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 915341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915341
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:3])=[O:2].IC.[C:26]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:26][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

Produkt 1

HCID 69231753ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate (1.0 g, 3.23 mmol) and iodomethane (2.5 mL, 40.2 mmol) in DMF (25 mL) was treated with Cs2CO3 (3.26 g, 10 mmol) and stirred for 16 h. The reaction was quenched by addition of water and the solid was collected and dried to yield ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate (I13064-48) as a yellowish solid (1.1 g, 100%): 1H NMR (DMSO-d6) δ 1.03 (t, J=7.0 Hz, 3 H), 4.09 (s, 3 H), 4.18 (q, J=7.0 Hz, 2 H), 7.40-7.55 (m, 5 H), 7.90 (d, J=9.2 Hz, 1 H), 8.23 (dd, J=9.2, 2.3 Hz, 1H), 8.32 (d, J=2.3 Hz, 1 H); MS (EI) m/z 325.2 (MH+).

Aufarbeitung

  1. customThe reaction was quenched by addition of water
  2. customthe solid was collected
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6a8c455eba574f72baeaa63526bd216b
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265148B2

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