Triphenylphosphine → Methyl 6-[4-({[5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-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), triphenylphosphine (94 mg, 0.36 mmol) and [5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methanol (Example 9e) (0.11 mg, 0.36 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.064 mL, 0.36 mmol). The mixture was heated to 90° C. for 10 minutes and then allowed to stand overnight. The mixture was adsorbed onto silica gel and purified by chromatography (silica gel, 0-40% ethyl acetate in hexanes gradient elution followed by further purification (silica gel, 0-30% ethyl acetate in hexanes gradient elution) to afford methyl 6-[4-({[5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (53 mg, 26%). 1H-NMR (400 MHz, DMSO-d6) δ 8.81 (s, 2H), 8.55 (d, J=9 Hz, 1H), 8.28 (s, 1H), 8.18-8.10 (m, 3H), 7.73 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 4.93 (s, 2H), 4.08-3.99 (m, 1H), 3.94 (s, 3H), 2.45-2.34 (m, 4H), 2.15-2.02 (m, 1H), 1.99-1.89 (m, 1H).

Provenance & Evidence