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ChemicalBook CAS DataBase List 3-PHENYL-4-PICOLINE
19352-29-5

3-PHENYL-4-PICOLINE synthesis

13synthesis methods
3-CHLORO-4-METHYLPYRIDINE

72093-04-0

Phenylmagnesium bromide

100-58-3

3-PHENYL-4-PICOLINE

19352-29-5

Pd Catalyst 1 (12.6 mg, 0.045 mmol, calculated based on the molar concentration of Pd) and 3-chloro-4-methylpyridine (0.2 mmol) were added to a Schlenk tube equipped with a magnetic stir bar. Anhydrous toluene (2.0 mL) and phenylmagnesium bromide (0.3 mmol, 1.5 equiv) were added sequentially under nitrogen protection. The reaction mixture was heated to 140 °C and the reaction was stirred at this temperature until complete consumption of 3-chloro-4-methylpyridine was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the reaction mixture was purified by silica gel column chromatography to afford the target product 3-phenyl-4-methylpyridine.

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Yield:19352-29-5 92%

Reaction Conditions:

with 4,5-dimethyl-3-(2-phenoxyphenyl)-1-(2,4,6-trimethylbenzyl)imidazolium chloride;palladium diacetate;caesium carbonate in 1,4-dioxane at 90; for 18 h;Inert atmosphere;Suzuki-Miyaura Coupling;

References:

Kuriyama, Masami;Matsuo, Seira;Shinozawa, Mina;Onomura, Osamu [Organic Letters,2013,vol. 15,# 11,p. 2716 - 2719] Location in patent:supporting information

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