4-CYCLOPENTYLBENZENEBORONIC ACID synthesis

Yield:1609374-11-9 68%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾;sodium carbonate in 1,2-dimethoxyethane;water;Inert atmosphere;Reflux;Suzuki Coupling;

Steps:

Synthesis of 2-Chloro-4-(4-cyclopentylphenyl)pyridine.

A mixture of 2-chloro-4-iodopyridine (6.43 g, 26.3mmol), (4-cyclopentylphenyl)boronic acid (5.0 g, 26.3 mmol), Pd(Ph3P)4 (0.0.91 g 0.79 mmol), sodium carbonate (8.37g, 79 mmol), DME (257 mL) and water (64 mL) was degassed with nitrogen and then refluxed overnight. The reactionmixture was concentrated and extracted with ethyl acetate.The the ethyl acetat layer was dried on Na2SO4 and thenfurther purified by column chromatography using dichloromethane in hexanes and then vacuum distilled to give 2-Chloro-4-(4-cyclopentylphenyl)pyridine (4.6 g, 68 % yield)

References:

EP2730583,2014,A1 Location in patent:Paragraph 0187; 0188