Triphenylphosphine → Methyl 6-[4-({[3-(3,5-dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (100 mg, 0.36 mmol), [3-(3,5-dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (103 mg, 0.36 mmol), triphenyl phosphine (94 mg, 0.36 mmol), diisopropyl azodicarboxylate (0.07 mL, 0.36 mmol) and dichloromethane (3.6 mL) were placed in a microwave reaction tube, sealed and heated in a microwave reactor to 100° C. for 10 minutes. The solution was concentrated then slurried in a 3:7 mixture of acetone: hexane. The resulting off-white solid was purified by chromatography (silica gel, 3:7 acetone:hexanes) to provide methyl 6-[4-({[3-(3,5-dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (0.10 g, 52%). 1H NMR (400 MHz, DMSO-d6): δ 8.81 (s, 2H), 8.55 (d, J=9 Hz, 1H), 8.29 (d, J=2 Hz, 1H), 8.18-8.10 (m, 3H), 7.74 (d, J=9 Hz, 2H), 6.89 (d, J=9 Hz, 2H), 4.97 (s, 2H), 3.94 (s, 3H), 3.49 (septet, 7 Hz, 1H), 1.34 (d, J=7 Hz, 6H). ESI-LCMS m/z 548 (M+H)+.

Provenance & Evidence