Triphenylphosphine → 2-[4-(1-Methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-[1.8]Naphthyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenol (72 mg) in dioxane 1.5 ml, was added triphenyl phosphine (121 mg), [1,8]Naphthyridin-2-yl-methanol (69 mg) and di-t-butyl-diazacarboxalate (106 mg) and the reaction mixture heated at 60° C. for 24 h. The reaction mixture was poured into 1 N NaOH, extracted with methylene chloride, dried magnesium sulfate and concentrated. Purification via Prep TLC eluting with 15% methanol/70% ethyl acetate/15% hexanes provided the title compound (9.8 mg). 1H NMR (400 MHz, CDCl3) δ 9.13 (dd, J=4.2, 1.7 Hz, 1H), 8.45 (d, J=5.8 Hz, 2H), 8.23 (d, J=8.3 Hz, 1H), 7.21 (dd, J=8.5, 2.1 Hz, 1H), 7.79 (d, J=8.7 Hz, 1H), 7.57 (s, 1H), 7.52 (m, 1H), 7.37 (d, J=9.1 Hz, 2H), 7.16 (d, J=6.2 Hz, 2H), 7.01 (d, J=8.7 Hz, 2H), 5.47 (s, 2H) 3.94 (s, 3H); MS: (M+H m/z=394.0).

Provenance & Evidence