Sodium Bicarbonate → HCID 58099175, compound

Participants

Reaction Steps

To a solution 6-Bromo-2-methylquinoline (17.4 g; 0.078 mol) in 2-ethoxyethanol (100 ml) was added tetrakis(triphenylphosphine) palladium (2.7 g; 0.0023 mol) and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 5 minutes. 2-Thienylboronic acid (10.0 g; 0.078 mol) was added followed by ethoxyethanol (70 ml). Sodium hydrogencarbonate (20 g; 0.24 mol) in water (100 ml) was added and the reaction mixture was magnetically stirred and heated under nitrogen at 90° C. for 16 h. The cooled reaction mixture was filtered through a pad of Celite hyflo supercel and then extracted with dichloromethane (2×150 ml), after addition of de-ionised water. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and solvent removed to give a light brown liquid. The liquid was distilled under reduced pressure to remove ethoxy ethanol. The residue was triturated with diethyl ether and cooled in the refrigerator to give an off white solid, 10.6 g (61%); Mp 87° C. (DSC, onset). Elemental analysis: Found C, 74.72; H 4.92; N, 6.12; S 13.43; C14H11NS requires C, 74.63; H 4.92; N, 6.21; and S, 14.24%.

Provenance & Evidence