Tributylvinyltin → 2-Benzyl-4-vinylisoindoline

HRID 389199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389199
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2Br)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([Sn](CCCC)(CCCC)C=C)[CH2:19]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH:18]=[CH2:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 81998TributylvinyltinHCID 529881582-Benzyl-4-bromo-2,3-dihydro-1H-isoindole

Produkt 1

HCID 574311892-Benzyl-4-vinylisoindoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2-benzyl-4-bromoisoindoline (16.7 g, 58.0 mmol) and tributyl(vinyl)tin (20.3 mL, 69.6 mmol) in PhMe (400 mL) was degassed by bubbling nitrogen gas through the solution for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) (1.30 g, 1.16 mmol) was added, and the resulting solution heated in a 100° C. oil bath, under nitrogen for 24 hours. The contents of the reaction flask were cooled, evaporated and subjected to flash column chromatography, eluting with hexane/ethyl acetate 95/5 to give the title compound as a pale oil that turned pink on standing. LRMS (ESI) m/z 236 [(M+H)+; calcd for C17H18N: 236].

Aufarbeitung

  1. customby bubbling nitrogen gas through the solution for 15 minutes
  2. temperatureThe contents of the reaction flask were cooled
  3. customevaporated
  4. washeluting with hexane/ethyl acetate 95/5

Quellen und Nachweise

ORD-Eintrag
ord-e64295767a8846c19852f0a3c2db7725
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377874B2

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