Potassium Phosphate, Tribasic → 5-[3-(2-Ethyl-3-formylphenyl)-1,2,4-thiadiazol-5-yl]-2-(2-methylpropyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile (D60) (500 mg), 2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (D5) (424 mg) and tripotassium phosphate (988 mg) in N,N-dimethylformamide (DMF) (4 mL) and water (1 mL) stirred under nitrogen was added Pd(Ph3P)4 (179 mg). The mixture was sealed and heated under microwave at 120° C. for 15 min. After cooling the reaction, the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulphate, concentrated and purified by column chromatography to give 5-[3-(2-ethyl-3-formylphenyl)-1,2,4-thiadiazol-5-yl]-2-(2-methylpropyl)benzonitrile (D63) (520 mg). δH (CDCl3, 400 MHz): 1.00 (6H, d), 1.37 (3H, t), 2.81 (2H, d), 3.38 (2H, q), 4.11 (1H, m), 7.48 (2H, m), 8.02 (1H, d), 8.14 (2H, m), 8.30 (1H, d), 10.48 (1H, s). MS (ES): C22H21N3OS requires 375. found 376.1 (M+H+).

Provenance & Evidence