Methyl iodide → 1-Acetyl-6-bromo-5-methoxyindoline

HRID 2214751

Reaktionsgleichung

Reaktionsgleichung von HRID 2214751
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Produkt 1

HCID 219483751-Acetyl-6-bromo-5-methoxyindolineAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 1-acetyl-6-bromoindolin-5-ol (Tetrahedron 1973, 29(8), 1115; 40 g, 0.15 mole) in DMF (500 ml) was treated with K2CO3 (61 g, 0.45 mole) and iodomethane (11.7 ml, 0.19 mole) and maintained at room temperature for 20 h, then concentrated under vacuum to 200 ml. The residue was treated with water (200 ml) and the precipitate filtered off, dried and recrystallised from EtOAc to afford the title compound as a white solid (35.7 g, 85%). MH+ 270/272.

Aufarbeitung

  1. concentrationconcentrated under vacuum to 200 ml
  2. additionThe residue was treated with water (200 ml)
  3. filtrationthe precipitate filtered off
  4. customdried
  5. customrecrystallised from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-5f997226f28c48008664d4de881b219d
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109201B2

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