Reaktion #2242

Reaktionsgleichung

2-(3,4-Dimethoxybenzenesulphonyl)-4-bromoisoindoline

triethylamine

2-ethynylpyridine

2-ethynylpyridine

→

title compound

Ausbeute 12.5%

2-(3,4-Dimethoxybenzenesulphonyl)-4-(2-pyrid-2-ylethynyl)isoindoline

Ausbeute 12.5%

Lösungsmittel

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheating
2. 2
   Filtrationfiltered through a pad of silica
3. 3
   Sonstigethe filtrate evaporated in vacuo
4. 4
   Sonstigeto yield a yellow residue
5. 5
   SonstigePurification by column chromatography
6. 6
   Wascheneluting with a 20-100% ethyl acetate in hexane gradient

Vorschrift

2-(3,4-Dimethoxybenzenesulphonyl)-4-bromoisoindoline (0.19 g), triethylamine (0.10 ml), 2-ethynylpyridine(0.06 g) and bis (triphenylphosphine)palladium(II)chloride (10%) in anhydrous N,N-dimethylformamide(2 ml) were stirred together under an inert atmosphere and heated to 90° C. After 20 hours further 2-ethynylpyridine(0.12 g) and palladium catalyst (20%) were added and heating continued for 3 days. The reaction mixture at room temperature was diluted with ethyl acetate, filtered through a pad of silica and the filtrate evaporated in vacuo to yield a yellow residue. Purification by column chromatography, eluting with a 20-100% ethyl acetate in hexane gradient afforded the title compound (25 mg).

Quelle