Reaktion #171855

Reaktionsgleichung

8-Bromo-2-isopropyl-2H-1,2,4-triazol-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

dimethylformamide

→

8-cyano-2-isopropyl-2H-1,2,4-triazol-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Ausbeute 71.3%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added to a CEM microwave vial
2. 2
   SonstigeThe mixture was thoroughly purged with nitrogen
3. 3
   Sonstigethe vial was sealed immediately
4. 4
   SonstigeThe reaction was submitted to MW irradiation at 60 W for 15 minutes (T=175° C.)
5. 5
   Filtrationfiltered through celite
6. 6
   Waschenwashed with saturated NH4Cl
7. 7
   Trocknendried with MgSO4
8. 8
   Einengenconcentrated
9. 9
   Sonstigepurified by flash chromatography (0-100% EtOAc in hexanes)

Vorschrift

8-Bromo-2-isopropyl-2H-1,2,4-triazol-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (330 mg, 0.84 mmol) and degassed dimethylformamide (4.2 mL) were added to a CEM microwave vial. The mixture was thoroughly purged with nitrogen. Zinc cyanide (99.0 mg, 0.84 mmol, 1.0 equiv.) and Pd(PPh3)4 (48.7 mg, 0.04 mmol, 0.05 equiv.) were added to the reaction mixture in one portion and the vial was sealed immediately. The reaction was submitted to MW irradiation at 60 W for 15 minutes (T=175° C.). The mixture was diluted with methylene chloride, filtered through celite, and washed with saturated NH4Cl. The organic layers were combined, dried with MgSO4 and concentrated. The crude mixture was loaded onto silica gel and purified by flash chromatography (0-100% EtOAc in hexanes) to give 202 mg (71.3% yield) of 8-cyano-2-isopropyl-2H-1,2,4-triazol-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene a yellow solid.

Quelle