Tributylphosphine → N-cyclopropyl-3-({4-[(4-methoxypyridin-2-yl)methoxy]benzoyl}amino)-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-cyclopropyl-3-[(4-hydroxybenzoyl)amino]-4-methylbenzamide (200 mg, 0.64 mmol) and 4-methoxy-2-hydroxymethylpyridine (500 mg, 3.6 mmol) in dry THF (25 mL) under an argon atmosphere was added successively tributylphosphine (500 mg, 2.5 mmol) and di-isopropyl azodicarboxylate (500 mg, 2.5 mmol). The mixture was stirred at 20° C. for 16 hours, then the solvent was evaporated at reduced pressure and the residue purified by silica column chromatography, eluting with a gradient of 0 to 10% methanol in ethyl acetate to give the title compound as a white solid (100 mg); NMR Spectrum: (DMSOd6) 1.55 (m, 2H), 1.65 (m, 2H), 2.25 (s, 3H), 2.85 (m, 1H), 3.85 (s, 3H), 5.20 (s, 2H), 6.95 (dd, 1H), 7.05 (d, 1H), 7.15 (d, 2H), 7.30 (d, 1H), 7.60 (dd, 1H), 7.80 (s, 1H), 7.95 (d, 2H), 8.35 (d, 1H), 8.40 (broad s, 1H), 9.80 (s, 1H); Mass Spectrum: M+H+ 432.

Provenance & Evidence