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

HRID 2118118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118118
[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-carboxylateAusbeute 105 %

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 as a yellowish solid (1.1 g, 100%): 1H NMR (DMSO-d6) δ 1.03 (t, J=7.0 Hz, 3H, 4.09 (s, 3H, 4.18 (q, J=7.0 Hz, 2H, 7.40-7.55 (m, 5H, 7.90 (d, J=9.2 Hz, 1H, 8.23 (dd, J=9.2, 2.3 Hz, 1H, 8.32 (d, J=2.3 Hz, 1H; 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-a42accc70b634a13bdf0929eeea1041d
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442805B2

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