Reaktion #70603

Reaktionsgleichung

Compound 10

4-chloro-2-(3,4-dimethoxy-benzyl)-7-[4-(1R)-(1-phenyl-ethyl)-piperazin-1-yl]-isoindole-1,3-dione

sodium acetate

methyl vinylsulfone

→

Compound 62

Ausbeute 19.4%

2-(3,4-dimethoxy-benzyl)-4-(2-methanesulfonyl-vinyl)-7-[4-(1R)-(1-phenyl-ethyl)-piperazin-1-yl]-isoindole-1,3-dione

Ausbeute 19.4%

Lösungsmittel

dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 10 mL sealed tube
2. 2
   workup.ADDITIONThe tube was charge with argon
3. 3
   Sonstigesealed
4. 4
   TemperaturThe mixture was cooled to room temperature
5. 5
   Sonstigepurified via flash chromatography (230-400 mesh silica gel 60, gradient 90:10-50:50 hexanes:ethyl acetate)

Vorschrift

A 10 mL sealed tube was charged with Compound 10 (100.0 mg, 0.19 mmol), sodium acetate (22.0 mg, 0.27 mmol), bis(tri-t-butylphosphine)palladium (0) (13.0 mg, 0.03 mmol), methyl vinylsulfone (0.02 ml, 0.23 mmol), and dimethylacetamide (1.0 mL). The tube was charge with argon and sealed. The mixture was heated at 150° C. for 24 h. The mixture was cooled to room temperature and purified via flash chromatography (230-400 mesh silica gel 60, gradient 90:10-50:50 hexanes:ethyl acetate) to give 21.7 mg (19%) of Compound 62 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.44 (d, J=15.6, 1 H), 7.48-7.53 (m, 5 H), 7.01-7.08 (m, 3 H), 6.70-6.90 (m, 3 H), 4.64 (s, 2 H), 4.42 (q, J=6.9 Hz, 1 H), 3.94 (s, 3 H), 3.86 (s, 3 H), 3.33-3.80 (m, 8 H), 3.07 (s, 3 H), and 1.86 (d, J=6.7 Hz, 3 H); MS (ES+) 590 (M+1).

Quelle