Cesium carbonate → 5-[5-(2-Ethyl-3-formylphenyl)-1,3-thiazol-2-yl]-2-(2-methylpropyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(5-bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D91) (1.1 g), 2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (D5) (443 mg) and Cs2CO3 (1.12 g) in 1,2-dimethoxyethane (DME) (15 mL) and water (3 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (2.80 g) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 1.5 h. After cooling the reaction, the reaction mixture was filtered through silica gel and the filtrate was washed with aqueous saturated ammonium chloride and saturated brine. The organic phase was collected and dried over anhydrous sodium sulphate. After concentration, the crude product was purified by column chromatography to give 5-[5-(2-ethyl-3-formylphenyl)-1,3-thiazol-2-yl]-2-(2-methylpropyl)benzonitrile (D92) (1.2 g). MS (ES): C23H22N2OS requires 374. found 375.1 (M+H+).

Provenance & Evidence