반응 #693872

반응 방정식

toluene methanol

2-cyanophenylboronic acid pinacol ester

2-bromo-4,6-dimethylaniline

potassium carbonate

→

3,5-dimethyl-6-phenanthridinamine

수율 82.0%

반응 조건

후처리

1. 1
   기타The solvents were degassed
2. 2
   온도the reaction mixture heated
3. 3
   온도to reflux for 48 hours
4. 4
   온도After cooling
5. 5
   여과filtered
6. 6
   기타the organics evaporated
7. 7
   기타crude product was purified
8. 8
   workup.ADDITIONtreated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants
9. 9
   기타The pure product was collected
10. 10
    농축concentrated

실험 절차

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).

출처