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

HRID 352355

Reaction equation

HRID 352355 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 219483751-Acetyl-6-bromo-5-methoxyindolineYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-1209a2796f0e4beea1373760462eba3d
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Linked notes

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