تفاعل #44288

معادلة التفاعل

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

CH2Cl2

triethylamine

→

desired product

المردود 88.0%

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

المردود 88.0%

المذيبات

DMAC

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was degassed
2. 2
   أخرىThe reaction mixture was degassed again
3. 3
   ترشيحthe reaction mixture was filtered through a celite pad
4. 4
   غسيلwashed with 5.0 ml of CH2Cl2
5. 5
   تركيزThe solvents were concentrated under reduced pressure
6. 6
   أخرىThe resulting residue was purified via flash column chromatography
7. 7
   غسيلeluted with 1-3% 7N

الإجراء التجريبي

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

المصدر