Triphenylphosphine → Methyl 6-[4-({[5-cyclopropyl-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 (81 mg, 0.29 mmol), triphenylphosphine (84 mg, 0.32 mmol) and [5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methanol (83 mg, 0.29 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.058 mL, 0.32 mmol) dropwise. The solution was heated in a microwave reactor at 90° C. for 10 minutes and then allowed to stand overnight. The solution was adsorbed onto silica gel and purified by chromatography (silica gel, 0-1.25% methanol in chloroform gradient elution) to afford methyl 6-[4-({[5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (70 mg, 44%). 1H-NMR (400 MHz, CDCl3) δ 8.60 (s, 2H), 8.39-8.33 (m, 2H), 8.22 (d, J=9 Hz, 1H), 8.01-7.96 (m, 2H), 7.60 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 4.90 (s, 2H), 4.09 (s, 3H), 2.22-2.15 (m, 1H), 1.33-1.13 (m, 4H).

Provenance & Evidence