Triphenylphosphine → Methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (0.10 mg, 0.36 mmol), [5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol (0.11 mg, 0.36 mmol) and triphenylphosphine (0.10 mg, 0.39 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.071 mL, 0.39 mmol) slowly. The solution was heated in a microwave reactor at 90° C. for 10 minutes and then was adsorbed onto silica gel and purified by chromatography (silica gel, 0-45% ethyl acetate in hexanes gradient elution) to afford methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (76 mg, 37%). 1H-NMR (400 MHz, DMSO d6) δ 8.55 (d, J=8 Hz, 1H), 8.28 (s, 1H), 8.18-8.10 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.63-7.51 (m, 3H), 6.96 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.93 (s, 3H), 3.58-3.50 (m, 1H), 2.11-2.03 (m, 2H), 1.84-1.64 (m, 6H).

Provenance & Evidence