Sodium Carbonate → 5-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dimethoxyphenylboronic acid (217 mg, 1.19 mmol, 1.2 equiv) (Step 1.8) in EtOH (0.5 mL) was added dropwise to a mixture of 5-bromo-quinoline-8-carboxylic acid (Step 159.3) (250 mg, 0.99 mmol), PdCl2(dppf) (22 mg, 0.03 mmol, 0.03 equiv), Na2CO3 (2M solution in H2O, 1 mL, 3.97 mmol, 4 equiv) in toluene (5 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 1 h, allowed to cool to rt, diluted with EtOAc and H2O, basified by addition of a 2N aqueous solution of NaOH (2 mL), filtered through a pad of celite and the filtrate was extracted with EtOAc. The aqueous layer was separated and acidified to pH 5. The resulting precipitate was collected by vacuum filtration to provide 248 mg of the title compound as a white solid: ESI-MS:310.1 [M+H]+; tR=4.06 min (System 1).

Provenance & Evidence