Methyl iodide → 6-Bromo-3-hydroxy-3-methylindolin-2-one

HRID 1476186

Reaction equation

HRID 1476186 reaction equation
C[Mg]I.[Mg].[CH3:5]I.[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12](=[O:18])[C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1>C(OCC)C.C1COCC1>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([OH:18])([CH3:5])[C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 957161H-Indole-2,3-dione, 6-bromo-HCID 5462224MagnesiumHCID 178418373HCID 178418373, compound

Product 1

HCID 665802586-Bromo-3-hydroxy-3-methylindolin-2-oneYield 98.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a ice-cold solution of methyl magnesium iodide prepared from magnesium (1.7 g, 70.78 mmoles) and methyl iodide (4.40 ml, 70.78 mmoles) in diethyl ether (60 ml), 6-bromoisatin (4 g, 17.69 mmoles) in THF (120 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dilute HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as brown solid (4.2 g, 93% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 10.34(s,1H), 7.23(t, J=7.9Hz, 1H), 7.14(dd, J=7.9,1.7Hz, 1H), 6.93(d, J=1.6Hz, 1H), 5.92(s, 1H), 1.33(s, 3H).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-723d87fac3a54d2f8cedaa4512dd740d
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Linked notes

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