Methyl iodide → Methyl 4-[3-methoxy6-nitroindazol-1-ylmethyl]-3-methoxybenzoate

HRID 275147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275147
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[O:25][CH3:26])[N:3]=1.[Na].I[CH3:29]>CO.C(OCC)(=O)C>[CH3:29][O:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[O:25][CH3:26])[N:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 178497911HCID 178497911, Verbindung

Produkt 1

HCID 23365859Methyl 4-[3-methoxy6-nitroindazol-1-ylmethyl]-3-methoxybenzoateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Indazole (T) (1.68 g.) was added to a solution of sodium (0.108 g.) in methanol (1.0 ml.). After stirring for 5 minutes, iodomethane (0.32 ml.) was added and stirring continued for 18 hours. The mixture was diluted with ethyl acetate, washed with water and brine, then dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (130 g.), eluting with 2:98 v/v ethyl acetate:dichloromethane to give methyl 4-[3-methoxy-6-nitroindazol-1-ylmethyl]-3-methoxybenzoate (U) (0.481 g., 28%) as a yellow solid, with satisfactory NMR spectral data.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (130 g.)
  7. washeluting with 2:98 v/v ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-46b76d47b2244b49ac455d5e29c9d5de
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391758

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