Reacción #2156971

Ecuación de reacción

6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

cyclopropylboronic acid

→

6-Cyclopropyl-3,4-dihydro-2H-isoquinolin-1-one

Rendimiento 97.2%

Disolventes

toluene

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled
2. 2
   Filtraciónfiltered
3. 3
   Lavadowashed with toluene
4. 4
   OtroThe organic phase was partitioned
5. 5
   Lavadowashed with water and brine
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated to an oil
9. 9
   workup.ADDITIONAddition of hexanes

Procedimiento

To a round bottomed flask charged with 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one (16.9 g, 74.7 mmol), cyclopropylboronic acid (9.45 g, 1.5 equiv), tricyclohexylphosphine (1.04 mg, 0.025 equiv), and K3PO4 hexahydrate (50 g, 2 equiv) in toluene (210 mL) and H2O (15 mL) was added Pd(OAc)2 (100 mg, 0.05 equiv).The combined mixture was heated for 4 h at 100° C. The reaction mixture was cooled, filtered and washed with toluene. The organic phase was partitioned and washed with water and brine, dried over Na2SO4, filtered and concentrated to an oil. Addition of hexanes produced 6-Cyclopropyl-3,4-dihydro-2H-isoquinolin-1-one as a tan solid (13.6 g). MS (ESI) 187.1 (M+H)+.

Fuente