Succinic Acid → 2-{4-[1-Methyl-4-(2-methyl-pyridin-4-yl)-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{4-[4-(2-Chloro-pyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline (100 mg) in dioxane (1.2 ml) was added methyl boroxine (0.066 ml), palladium tetrakis (41 mg) and 2N sodium carbonate solution (0.234 ml). The reaction mixture was heated at 100° C. for 8 h, poured into 1 N NaOH, extracted with chloroform, dried magnesium sulfate, filtered and concentrated. Prep TLC run with 3% methanol/0.5% saturated ammonium hydroxide/80% ethyl acetate in hexanes provided the free base material. The produce was stirred in ethyl acetate and 2 eq. of succinic acid was added to give a white precipitate which was filtered to provide the title compound as a white solid succinate salt (20 mg). 1H NMR (400 MHz, DMSO) δ 8.40 (d, J=8.3 Hz, 2 H), 8.25 (d, J=5.0 Hz, 2 H), 8.07 (s, 1H), 8.00 (t, J=7.9 Hz, 2 H), 7.77 (t, J=6.6 Hz, 1 H), 7.67 (d, J=8.7 Hz, 2H), 7.60 (t, J=6.6 Hz, 1 H), 7.29 (d, J=9.1 Hz, 2H), 7.03 (m, 3 H), 6.92 (m, 1H), 5.35 (s, 2H), 3.85 (s, 3H), 2.37 (s, 4H) 2.31 (s, 3H); MS: (M+H m/z=407.0).

Provenance & Evidence