반응 #92475

반응 방정식

3-bromo-5-methylpicolinic acid

K2CO3

2H-1,2,3-triazole

DMF

→

title compound

수율 35.0%

5-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile

수율 35.0%

5-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile

수율 27.0%

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   추출extracted with EtOAc (2×)
3. 3
   건조The combined organics were dried (Na2SO4)
4. 4
   농축concentrated
5. 5
   기타Purification via silica gel chromatography (5-60% EtOAc in hexanes)

실험 절차

To 3-bromo-5-methylpicolinic acid (1.5 g, 7.6 mmol) in DMF (19 mL) was added K2CO3 (1.2 g, 8.4 mmol) and 2H-1,2,3-triazole (440 μL, 7.6 mmol). The mixture was heated to 100° C. for 16 h, cooled to room temperature and extracted with EtOAc (2×). The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (5-60% EtOAc in hexanes) gave the title compound (490 mg, 35%)1H NMR (500 MHz, Chloroform-d) 8.58-8.53 (m, 1H), 8.29-8.24 (m, 1H), 7.98 (s, 2H), 2.54 (s, 3H) and 5-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile (387 mg, 27%).

출처