Triphenylphosphine → HCID 59321568, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [5-cyclopropyl-3-(2,6-dichlorophenyl) -4-isoxazolyl]methanol (0.10 g, 0.36 mmol), methyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate (0.10 g, 0.36 mmol) and triphenylphosphine (0.10 g, 0.39 mmol) in dichloromethane (2.5 mL) was added diisopropyl azodicarboxylate (0.071 mL, 0.39 mmol) dropwise. The solution was heated in a microwave reactor to 90° C. for 10 minutes and then allowed to sit overnight. The solution was adsorbed onto silica gel and purified by chromatography (silica gel, 0-45% ethyl acetate in hexanes gradient elution) to afford methyl 6-[4-({[5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (62 mg, 32%). 1H-NMR (400 MHz, DMSO-d6) δ 8.55 (d, J=9 Hz, 1H), 8.28 (s, 1H), 8.18-8.10 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.62-7.50 (m, 3H), 6.95 (d, J=9 Hz, 2H), 4.93 (s, 2H), 3.93 (s, 3H), 2.50-2.42 (m, overlapping DMSO ˜1H), 1.20-1.12 (m, 4H). LRMS (APCI) m/z 545 (M+H)+.

Provenance & Evidence