Reacción #44288

Ecuación de reacción

6-[(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl]quinoline

CH2Cl2

triethylamine

→

desired product

Rendimiento 88.0%

1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbonitrile

Rendimiento 88.0%

Disolventes

DMAC

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was degassed
2. 2
   OtroThe reaction mixture was degassed again
3. 3
   Filtraciónthe reaction mixture was filtered through a celite pad
4. 4
   Lavadowashed with 5.0 ml of CH2Cl2
5. 5
   ConcentraciónThe solvents were concentrated under reduced pressure
6. 6
   OtroThe resulting residue was purified via flash column chromatography
7. 7
   Lavadoeluted with 1-3% 7N

Procedimiento

To a suspension of 6-[(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl]quinoline (1.0 g, 2.93 mmol) in DMAC (70 ml) were added zinc cyanide (413 mg, 3.52 mmol). The reaction mixture was degassed then PdCl2(dppf).CH2Cl2 (240 mg, 0.29 mmol) was added followed with triethylamine (0.828 ml) at R.T. The reaction mixture was degassed again. After heating at 85° C., the reaction mixture was filtered through a celite pad and washed with 5.0 ml of CH2Cl2. The solvents were concentrated under reduced pressure. The resulting residue was purified via flash column chromatography eluted with 1-3% 7N N3 in MeOH:CH2Cl2 to give the desired product (740 mg, 88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.28 (s, 2H) 7.55 (dd, J=8.34, 4.29 Hz, 1H) 7.81 (dd, J=8.72, 2.15 Hz, 1H) 7.99-8.04 (m, 2H) 8.33-8.37 (m, 1H) 8.91 (dd, J=4.04, 1.77 Hz, 1H) 9.41 (s, 1H) APCI (Mz+1) 288.2

Fuente