Sodium Carbonate → Ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]-2-quinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of crude [4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid (76 mg, 0.18 mmol), ethyl 6-bromo-2-quinolinecarboxylate (42 mg, 0.15 mmol), tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.0006 mmol) in 1,2-dimethoxyethane (0.8 mL), and 2 M sodium carbonate (0.65 mL) was heated in a 70° C. oil bath for 1.5 hours. The solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with magnesium sulfate filtered and concentrated. The residue was purified by silica gel chromatography (hexane to 2:5 ethyl acetate:hexanes gradient elution) to give 20 mg (22% as 0.4 ethyl acetate) of ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]-2-quinolinecarboxylate. 1H NMR (400 MHz, CDCl3): δ 8.38-8.32 (m, 2H), 8.21 (d, J=9 Hz, 1H), 7.98 (s, 1H), 7.96 (d, J=2 Hz, 1H), 7.59 (d, J=8 Hz, 2H), 7.43-7.32 (m, 5H), 4.57 (q, J=7 Hz, 2H), 3.82 (s, 2H), 3.07 (septet, J=7 Hz, 1H), 1.50 (t, J=7 Hz, 3H), 1.27 (d, J=7 Hz, 6H).

Provenance & Evidence