1H-Indole-2,3-dione, 6-bromo- → 6-Bromo-3-hydroxy-3-methylindolin-2-one

HRID 2209297

Reaktionsgleichung

Reaktionsgleichung von HRID 2209297
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:13][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([OH:12])([CH3:13])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 957161H-Indole-2,3-dione, 6-bromo-HCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 665802586-Bromo-3-hydroxy-3-methylindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 6-bromoisatin (255 mg, 1.13 mmol) in THF (3.0 mL) was added methylmagnesium bromide (1.12 mL, 3.39 mmol, 3M in ether). The solution was stirred at room temperature for 2 hours. The solution was cooled to 0° C. and was quenched with a saturated solution of ammonium chloride. The aqueous layer was extracted with EtOAc (3×), washed with brine, dried over MgSO4, filtered and concentrated to afford 6-bromo-3-hydroxy-3-methylindolin-2-one 7.45. The solid was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 7.24 (d, J=7.9 Hz, 1H), 7.15 (dd, J=7.9, 1.8 Hz, 1H), 6.94 (d, J=1.8 Hz, 1H), 5.94 (s, 1H), 1.34 (s, 3H).

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C.
  2. customwas quenched with a saturated solution of ammonium chloride
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f9007e33f0d04814a17ca686ccb756da
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

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