Reacción #425364

Ecuación de reacción

5-bromo-imidazo[1,2-f]phenanthridine

4-isopropylphenylboronic acid

potassium carbonate

triphenylphosphine

→

5-(4-isopropylphenyl)-imidazo[1,2-f]phenanthridine

Rendimiento 77.7%

Disolventes

methylene chloride

1.2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed by brine
2. 2
   Secadodried over sodium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe crude mixture was purified by chromagraphy on silica gel

Procedimiento

A three neck 1 L round bottom flask was charged with 5-bromo-imidazo[1,2-f]phenanthridine (4.55 g, 15.31 mmole), 4-isopropylphenylboronic acid (3.59 g, 21.89 mmole), potassium carbonate (2N aqueous soln., 27 ml), Pd(OAc)2 (223 mg, 0.99 mmole), triphenylphosphine (1.044 g, 3.98 mmole) and 100 ml of 1.2-dimethoxyethane. The reaction mixture was heated to 80° C. under nitrogen for 17 hrs. The reaction mixture was diluted with methylene chloride and washed by brine. The organic fractions were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by chromagraphy on silica gel using hexane/ethyl acetate (80/20) to obtain pure 5-(4-isopropylphenyl)-imidazo[1,2-f]phenanthridine (4 g, 77%).

Fuente