Water → 5-(5-Bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile

Participants

Reaction Steps

To a suspension of 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (D59) (600 mg), 2,5-dibromo-1,3-thiazole (767 mg), and Cs2CO3 (1028 mg) in 1,2-dimethoxyethane (DME) (10 mL)/water (2 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (344 mg). The reaction mixture was sealed and heated under microwave at 120° C. for 4 h. After cooling the reaction, the mixture was diluted with ethyl acetate and filtered through silical gel. The filtrate was washed with aqueous saturated ammonium chloride and saturated brine. The organic phase was collected and dried over anhydrous sodium sulphate. The solvent was removed in vacuo to give the crude product, which was purified by column chromatography to afford 5-(5-bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D91) (400 mg). MS (ES): C14H13BrN2S requires 320. found 321.0 (M+H+).

Provenance & Evidence