Triphenylphosphine → HCID 69097659, Verbindung

HRID 1626934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626934
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15][C:16](=[O:32])[O:17][CH2:18][CH:19]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH3:14])[N:3]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH:33]=[CH2:34])=[N:3][C:4]([C@@H:13]([NH:15][C:16](=[O:32])[O:17][CH2:18][CH:19]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:14])=[CH:5]2

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 86665027(S)-(9H-fluoren-9-yl)methyl 1-(1,8-dichloroisoquinolin-3-yl)ethylcarbamate

Produkt 1

HCID 69097659HCID 69097659, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-(9H-fluoren-9-yl)methyl-1-(1,8-dichloroisoquinoline-3-yl)ethylcarbamate (346) (36 g, 77.7 mmol, 1.0 eq) in THF (300 mL) under argon, tributyl(vinyl)stannane (27 g, 85.5 mmol, 1.1 eq), Pd(OAc)2 (5.23 g, 23.3 mmol, 0.3 eq) and PPh3 (12.2 g, 46.6 mmol, 0.6 eq) were added, and the resulting mixture was stirred at reflux for 16 h. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2-30% ethyl acetate-petroleum ether) to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-vinylisoquinolin-3-yl)ethylcarbamate (347).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (2-30% ethyl acetate-petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-97a0883865cf42edaaccfc634d6a1ee6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785470B2

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