Benzyl Alcohol → Benzyl 1-methyl-oxindole-5-carboxylate

HRID 1976780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976780
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6](=[O:12])[CH2:5]2.C(N(CC)CC)C.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C[O:31][CH2:30]C1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:30]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:31])=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:12]

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24326665-Bromo-1-methyl-2-oxoindoline

Produkt 1

HCID 21998744Benzyl 1-methyl-oxindole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A solution of 5-bromo-1-methyl oxindole (3.75 g, 16.6 mmol) and triethylamine (3.48 mL) in THF (40 mL) was treated with benzyl alcohol (2.58 mL) and PdCl2(dppf) (300 mg), stirred under carbon monoxide (680 psi) at 130° C. for 16 hours, depressurized, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified on silica gel with 30% ethyl acetate/hexanes to provide 2.36 g of the desired product.

Aufarbeitung

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated
  3. customThe concentrate was purified on silica gel with 30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e1162bedb14248e2ae3d2451e161fd4e
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06228868B1

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