Reacción #91939

Ecuación de reacción

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran

S-Phos

K3PO4

4-bromo-N-methylaniline

→

title compound

Rendimiento 76.5%

4-(3,6-dihydro-2H-pyran-4-yl)-N-methylaniline

Rendimiento 76.5%

Disolventes

toluene H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe reaction mixture was filtered
2. 2
   Concentraciónconcentrated
3. 3
   OtroThe residue was purified by silica gel chromatography (PE:EtOAc=10:1)

Procedimiento

To a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (800 mg, 3.8 mmol), S-Phos (160 mg, 0.38 mmol), Pd2(dba)3 (72 mg, 0.08 mmol), and K3PO4 (96 mg, 3.8 mmol) in toluene/H2O (100 mL/20 mL) was added 4-bromo-N-methylaniline (712 mg, 3.84 mmol) under N2. After stirring at 115° C. overnight, the reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=10:1) to give 550 mg (76%) of the title compound as a yellow solid. [M+H] Calc'd for C12H15NO, 190. Found, 190.

Fuente