Reacción #595412

Ecuación de reacción

tert-butyl 3,6-dibromo-9H-carbazole-9-carboxylate

potassium phosphate tribasic

tricyclohexylphosphine

cyclopropyl boronic acid

→

crude product

tert-butyl 3,6-dicyclopropyl-9H-carbazole-9-carboxylate

Disolventes

EtOAc

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe vial was sparged with N2
2. 2
   workup.ADDITIONcharged with 0.22 mL
3. 3
   Otrodegassed toluene
4. 4
   OtroThe crude reaction mixture
5. 5
   Lavadowashed with brine (3×10 mL)
6. 6
   SecadoThe organic layer was dried over anhydrous Na2SO4
7. 7
   Otroevaporated

Procedimiento

Following a literature procedure (Petit et al., ChemMedChem 2009, 4, 261-275), tert-butyl 3,6-dibromo-9H-carbazole-9-carboxylate (0.0200 g, 0.0470 mmol), cyclopropyl boronic acid (0.0202 g, 0.235 mmol), palladium acetate (10 mol %, 0.0011 g, 0.00470 mmol), potassium phosphate tribasic (0.0350 g, 0.165 mmol), tricyclohexylphosphine (0.0026 g, 0.00941 mmol), water (12.2 μL) and a stir bar were combined in a sealed vial. The vial was sparged with N2 and charged with 0.22 mL degassed toluene. The mixture was stirred at 100° C. for 65 h. The crude reaction mixture was diluted with 10 mL EtOAc and washed with brine (3×10 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was used as is without further purification.

Fuente