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

HRID 1476186

반응식

HRID 1476186 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-723d87fac3a54d2f8cedaa4512dd740d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018375B2

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