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

Participants

Reaction Steps

To a solution of methyl 6-[4-({[3-(hydroxymethyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (25 mg, 0.058 mmol), N-(2,6-dichlorophenyl)-2,2,2-trifluoroacetamide (15 mg, 0.058 mmol) and triphenylphosphine (30 mg, 0.12 mmol) in dichloromethane was added di-tert-butyl azodicarboxylate (27 mg, 0.12 mmol). The solution was stirred at ambient temperature for approximately 1.5 hours and then was adsorbed onto silica gel and purified by chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient elution). The resulting mixture was further purified by chromatography (silica gel, 2% methanol in dichloromethane) to afford methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (10 mg, 26%). 1H-NMR (400 MHz, CDCl3) δ 8.36-8.33 (m, 2H), 8.22 (d, J=9 Hz, 1H), 8.06-8.01 (m, 2H), 7.71 (d, J=9 Hz, 2H), 7.42-7.29 (m, 3H), 7.11 (d, J=9 Hz, 2H), 5.05 (s, 2H), 5.04 (s, 2H), 4.05 (s, 3H), 3.27 (septet, J=7 Hz, 1H), 1.34 (d, J=7 Hz, 6H). LRMS (APCI) m/z 672 (M+H)+.

Provenance & Evidence