Réaction #693872

Équation de réaction

toluene methanol

2-cyanophenylboronic acid pinacol ester

2-bromo-4,6-dimethylaniline

potassium carbonate

→

3,5-dimethyl-6-phenanthridinamine

Rendement 82.0%

Conditions de réaction

Traitement

1. 1
   AutreThe solvents were degassed
2. 2
   Températurethe reaction mixture heated
3. 3
   Températureto reflux for 48 hours
4. 4
   TempératureAfter cooling
5. 5
   Filtrationfiltered
6. 6
   Autrethe organics evaporated
7. 7
   Autrecrude product was purified
8. 8
   workup.ADDITIONtreated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants
9. 9
   AutreThe pure product was collected
10. 10
    Concentrationconcentrated

Mode opératoire

Added together 2-cyanophenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) to a 125 mL of a 95/5 mixture of toluene/methanol. The solvents were degassed and the reaction mixture heated to reflux for 48 hours. After cooling, the reaction mixture was vacuum filtered and the organics evaporated and crude product was purified using silica gel column chromatography treated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants. The pure product was collected and concentrated to give 3,5-dimethyl-6-phenanthridinamine (9.1 g, 82% Yield).

Source