Triphenylphosphine → Methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of triphenylphosphine (160 mg, 0.611 mmol), [3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol (153 mg, 0.556 mmol) and methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate (155 mg, 0.556 mmol) in dichloromethane (1.5 mL) was added diisopropyl azodicarboxylate (0.110 mL, 0.611 mmol) dropwise. The solution was heated in a microwave reactor at 90° C. for 10 minutes and then purified by chromatography (silica gel, 0-25% acetone in hexanes gradient elution) to afford methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate (109 mg, 37%). 1H-NMR (400 MHz, DMSO-d6) δ 9.11 (s, 1H), 8.64 (s, 1H), 8.50 (s, 1H), 8.29-8.20 (m, 2H), 7.86 (d, J=9 Hz, 2H), 7.19 (d, J=9 Hz, 2H), 7.00-6.90 (m, 3H), 5.09 (s, 2H), 4.90 (s, 2H), 3.91 (s, 3H), 3.41 (septet, J=7 Hz, 1H), 2.14 (s, 6H), 1.28 (d, J=7 Hz, 6H).

Provenance & Evidence