Reacción #961251

Ecuación de reacción

(S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine

tri(o-tolyl)phosphine

triethylamine

Acrylonitrile

→

title compound

Rendimiento 71.1%

(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)acrylonitrile

Rendimiento 71.1%

Disolventes

MeCN

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed
2. 2
   Otroby bubbling argon through
3. 3
   Temperaturathe reaction mixture heated
4. 4
   Temperaturaat reflux temperature for 18 hours
5. 5
   Filtraciónfiltered through Celite
6. 6
   Otrothe solvents evaporated
7. 7
   Otroto give a brown solid
8. 8
   OtroThe crude product was purified by flash chromatography (2% [20% ammonia in MeOH] in DCM)

Procedimiento

A mixture of (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (preparation 1) (300 mg, 1.24 mmol), palladium (II) acetate (14 mg, 0.06 mmol), tri(o-tolyl)phosphine (75 mg, 0.25 mmol) and triethylamine (0.35 mL, 2.48 mmol) in MeCN (10 mL) was degassed by bubbling argon through. Acrylonitrile (0.12 mL, 1.87 mmol) was then added and the reaction mixture heated at reflux temperature for 18 hours. The reaction mixture was cooled to room temperature, filtered through Celite, and the solvents evaporated to give a brown solid. The crude product was purified by flash chromatography (2% [20% ammonia in MeOH] in DCM) to give the title compound as a red-brown oil (188 mg, 71%, mixture of cis and trans isomers).

Fuente