Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate → methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate

HRID 333377

Reaktionsgleichung

Reaktionsgleichung von HRID 333377
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:14].[Br:15][C:16]1[C:20]([CH3:22])([CH3:21])[O:19][C:18](=O)[CH:17]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>C1COCC1>[Br:15][C:16]1[C:20]([CH3:22])([CH3:21])[O:19]/[C:18](=[C:3]2/[C:2](=[O:14])[NH:1][C:9]3[C:4]/2=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=3)/[CH:17]=1

Komponenten

5

Edukt 3

HCID 2773516Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylateHCID 126719604-Bromo-5,5-dimethylfuran-2-oneHCID 23714775LiHMDS tetrahydrofuran

Produkt 1

HCID 58926238methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. stirred solution of methyl oxindole-5-carboxylate (421 mg, 2.2 mmol) and 4-bromo-5,5-dimethylfuran-2(5H)-one (382 mg, 2.0 mmol) in THF (10 mL), was added 1M LiHMDS/THF solution (4.4 mL, 4.4 mmol) under nitrogen. The mixture was stirred at 0° C. for 80 min, quenched with 2.5M H2SO4 (3 mL), and poured into 100 mL of water. The precipitates were filtered, washed with water, and dried in vacuo to give methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate as yellow solid. Yield: 408 mg, 56%.

Aufarbeitung

  1. customquenched with 2.5M H2SO4 (3 mL)
  2. additionpoured into 100 mL of water
  3. filtrationThe precipitates were filtered
  4. washwashed with water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-557b12f398bb4a36a7b59188670d8f55
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877923B2

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