반응 #823561

반응 방정식

Phenylboronic acid

2-bromo-5-methylpyridine

K2CO3

→

title compound

5-methyl-2-phenylpyridine

용매

CH3CN

반응 조건

후처리

1. 1
   기타at 90°
2. 2
   기타overnight
3. 3
   농축concentrated under reduced pressure
4. 4
   기타The residue was partitioned between brine and ethyl acetate
5. 5
   기타The organic layer was separated
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축the filtrate was concentrated under reduced pressure
9. 9
   기타The residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate)

실험 절차

Phenylboronic acid (732 mg, 6 mmol), 2-bromo-5-methylpyridine (1.03 g, 5.99 mmol), and Pd (PPh3)4 (350 mg, 0.303 mmol) were heated in 0.4 M K2CO3 (30 mL, 12 mmol) and CH3CN (30 mL) at 90° overnight. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and ethyl acetate. The organic layer was separated, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (m, 1H), 8.05 (m, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.68-7.71 (m, 1H), 7.37-7.50 (m, 3H), 2.34 (s, 3H); MS (APCI+) m/z 170 (M+H)+.

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