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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (31 mg, 0.11 mmol), 3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol (35 mg, 0.11 mmol) and triphenylphosphine (29 mg, 0.11 mmol) in dichloromethane (1 mL) was added diisopropyl azodicarboxylate (0.020 mL, 0.11 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and was then adsorbed onto silica gel and purified by chromatography (silica gel, 0-35% ethyl acetate in hexanes gradient elution) to afford methyl 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylate (14 mg, 22%). 1H-NMR (400 MHz, CDCl3) δ 8.33 (m, 2H), 8.21 (d, J=8 Hz, 1H), 8.03-7.99 (m, 2H), 7.63 (d, J=9 Hz, 2H), 7.40-7.28 (m, 3H), 6.91 (d, J=9 Hz, 2H), 4.09 (s, 3H), 3.89 (t, J=6 Hz, 2H), 3.19 (septet, J=7 Hz, 1H), 2.51 (t, J=6 Hz, 2H), 1.82-1.76 (m, 2H), 1.33 (d, J=7 Hz, 6H).

Provenance & Evidence