反応 #69873

反応方程式

4-bromo-2-methylpyridine

1H-pyrazole

1,10-phenanthroline

K2CO3

→

title compound

収率 92.0%

2-methyl-4-(1H-pyrazol-1-yl)pyridine

収率 92.0%

溶媒

toluene

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度The reaction mixture was cooled to rt
3. 3
   その他quenched with water (50 mL)
4. 4
   抽出extracted with dichloromethane (150 mL)
5. 5
   洗浄The organic layer was washed with brine
6. 6
   乾燥dried over anhydrous Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The crude product was purified flash column chromatography (eluent: 30% ethyl acetate in hexane)

実験手順

To a mixture of 4-bromo-2-methylpyridine [22282-99-1] (350 mg, 2.05 mmol), 1H-pyrazole (140 mg, 2.05 mmol), 1,10-phenanthroline (74 mg, 0.41 mmol) and K2CO3 (567 mg, 4.1 mmol) in toluene (2 mL), CuI (19 mg, 0.1 mmol) was added and the reaction mixture was heated at 120° C. for 70 h in a sealed tube. The reaction mixture was cooled to rt, quenched with water (50 mL) and extracted with dichloromethane (150 mL). The organic layer was washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified flash column chromatography (eluent: 30% ethyl acetate in hexane) to yield the title compound (300 mg, 92%). [1H NMR (300 MHz, CDCl3) ♀ ppm 8.53 (d, 1H), 8.02 (d, 1H), 7.77 (d, 1H), 7.55 (d, 1H), 7.44-7.40 (m, 1H), 6.52 (t, 1H), 2.62 (s, 3H); TLC Rf=0.28 (ethyl acetate/hexane 30:70)].

出典