Reacción #1129877

Ecuación de reacción

N-(4-Bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine

tricyclohexylphosphine

2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

potassium phosphate

→

title compound

4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine

Disolventes

toluene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was sealed
2. 2
   workup.STIRRINGstirred at 80° C. for 19 h
3. 3
   TemperaturaThe reaction was then cooled to RT
4. 4
   Otroquenched with EtOAc
5. 5
   Extracciónextracted into water
6. 6
   Lavadowashed once with brine
7. 7
   Secadodried over Mg2SO4
8. 8
   OtroThe crude mixture was then purified by reverse phase chromatography

Procedimiento

To a pressure vessel was added 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (900 mg, 5.36 mmol), potassium phosphate (3.0 g, 14.42 mmol), and 0.82 mL water. After stirring at RT for 15 minutes, N-(4-Bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (Step 1, 1.30 g, 4.12 mmol), palladium acetate (92 mg, 0.412 mmol), tricyclohexylphosphine (231 mg 0.824 mmol), and 21 ml toluene were added. The reaction was sealed and stirred at 80° C. for 19 h. The reaction was then cooled to RT, quenched with EtOAc and extracted into water, washed once with brine, and then dried over Mg2SO4. The crude mixture was then purified by reverse phase chromatography to yield the title compound as a dark red-brown oil. MS (M+H−)=278; Calc'd for C15H23N3O2=277.36.

Fuente