Triphenylphosphine → Methyl 7-[4-({[5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate (50 mg, 0.18 mmol), [5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methanol (54 mg, 0.18 mmol) and triphenylphosphine (52 mg, 0.20 mmol) in dichloromethane (1.5 mL) was added diisopropyl azodicarboxylate (0.035 mL, 0.20 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and allowed to stand at ambient temperature overnight. The next day the solution was adsorbed onto silica gel and purified by chromatography (first in 0-1.75% methanol in chloroform gradient elution then in 0-2% methanol in chloroform) to afford methyl 7-[4-({[5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate as a white solid (39 mg, 39%). 1H-NMR (400 MHz, DMSO-d6) δ 9.33 (s, 1H), 8.59 (s, 3H), 8.12 (s, 1H), 8.00-7.94 (m, 2H), 7.58 (d, J=9 Hz, 2H), 6.84 (d, J=9 Hz, 2H), 4.79 (s, 2H), 4.04 (s, 3H), 3.87-3.79 (m, 1H), 2.64-2.54 (m, 2H), 2.50-2.35 (m, 2H), 2.19-2.00 (m, 2H).

Provenance & Evidence