Stannane, tributyl(1-ethoxyethenyl)- → HCID 86694713, Verbindung

HRID 475165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475165
Br[C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:12].C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC>CN1C(=O)CCC1>[CH2:21]([O:20][C:18]([C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:12])=[CH2:19])[CH3:22]

Komponenten

4

Edukt 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86694712HCID 86694712, Verbindung

Produkt 1

HCID 86694713HCID 86694713, VerbindungAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 4-bromo-6-fluoro-1-methyl-1H-indazole (1.42 g, 6.25 mmol) and tributyl(1-ethoxyvinyl)stannane (2.74 mL, 8.13 mmol, 1.3 eq.) in NMP (24 mL) under an argon atmosphere was added Pd(0)(PPh3)4 (1.08 g, 0.94 mmol, 0.2 eq.). After the mixture was heated at 110° C. overnight, it was cooled and partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), and evaporated in vacuo. The crude was purified by SiO2 chromatography eluting with hexane:ethyl acetate (3:1) to afford 4-(1-ethoxyvinyl)-6-fluoro-1-methyl-1H-indazole as a yellow oil (1.24 g, 90%). MS (ESI): m/z=221.3 [M+1]+.

Aufarbeitung

  1. temperatureit was cooled
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe crude was purified by SiO2 chromatography
  7. washeluting with hexane:ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2c0f45ea40ad4f0387beee11373e21cf
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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