Dichloromethane → 4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole
Reaktionsgleichung
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[S:16][CH:17]=[C:18]([CH3:20])[N:19]=2)[N:3]=1.[CH2:21](N(CC)CC)[CH3:22].[B-](F)(F)(F)C=C.[K+].ClCCl>CC(O)C.C1COCC1>[CH3:20][C:18]1[N:19]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:21]=[CH2:22])=[N:3]2)[S:16][CH:17]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
A suspension of 2-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazole (0.414 g, 1.03 mmol) in IPA/THF (4:1; 15 mL) was degassed with argon, treated with triethylamine (0.433 mL, 3.10 mmol), potassium trifluoro(vinyl)borate (0.416 g, 3.10 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (0.0845 g, 0.103 mmol). The mixture was heated at 90° C. for 14 hours under argon. The mixture was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (10-75% EtOAc in hexanes) to provide 4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole (0.249 g, 80% yield) as an amber gum.
Aufarbeitung
- customwas degassed with argon
- filtrationThe mixture was filtered through glass fiber
- filtrationfilter paper
- concentrationconcentrated under reduced pressure
- custompurified by silica gel chromatography (10-75% EtOAc in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-a31ab11f0afc4773a5372ba13f582d0a
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08841455B2
Notizen zur Reaktion
Wird geladen…