Sodium Carbonate → HCID 58099177, compound

Participants

Reaction Steps

To a solution 6-Bromo-2-methylquinoline (4.7 g; 0.021 mol) in 2-ethoxyethanol (80 ml) was added tetrakis(triphenylphosphine) palladium (0.5 g; 0.0004 mol) and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 5 minutes. 2,4-Difluorophenylboronic acid (3.5 g; 0.022 mol) was added followed by ethoxyethanol (20 ml). Sodium carbonate (10 g; 0.094 mol) in water (50 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 (3×100 ml), after addition of de-ionised water. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and solvent removed to give the residue, which was triturated with ether and cooling in the refrigerator gave a solid. This was filtered off and dried under vacuum at 60° C. to give a colourless solid. Yield 3.9 g (72%). Mp 86° C. (DSC, onset). Elemental analysis: Found C, 73.76; H, 4.39; N, 5.38; C16H11NF2 requires C, 75.28; H, 4.34; and N, 5.49%.

Provenance & Evidence