Reaktion #166653

Reaktionsgleichung

2-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazole

triethylamine

potassium trifluoro(vinyl)borate

dichloromethane

→

4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole

Ausbeute 80.5%

Lösungsmittel

IPA THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed with argon
2. 2
   FiltrationThe mixture was filtered through glass fiber
3. 3
   Filtrationfilter paper
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Sonstigepurified by silica gel chromatography (10-75% EtOAc in hexanes)

Vorschrift

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.

Quelle