Potassium Phosphate, Tribasic → N-(6'-ethoxy-5-morpholino-2,3'-bipyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine

Participants

Reaction Conditions

Reaction Steps

N-(2-Chloro-5-morpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)-quinolin-4-amine (32.7 mg, 0.07 mmol), 6-ethoxypyridin-3-ylboronic acid (14.1 mg, 0.084 mmol), tris(dibenzylideneacetone)dipalladium (0) (3.3 mg, 3.6 μmol), and tricyclohexylphosphine (2.1 mg, 7.5 μmol) were added to a flask then degassed and backfilled with argon. To the flask, 1,4-dioxane (0.5 mL) and aq. 1. 3M potassium phosphate tribasic (0.1 mL, 0.13 mmol) were added by syringe. The resulting reaction was heated to 90° C. and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on basic alumina (0-45% EtOAc in hexanes) to afford a light yellow solid as N-(6′-ethoxy-5-morpholino-2,3′-bipyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (500 MHz, CDCl3) δ ppm 8.71 (1H, d, J=4.9 Hz), 8.66 (1H, d, J=2.4 Hz), 8.10 (2H, m), 7.94 (2H, d, J=3.9 Hz), 7.68 (1H, m), 7.46 (1H, m), 7.01 (2H, ddd, J=13.4, 8.6, 2.4 Hz), 6.93 (1H, d, J=8.8 Hz), 6.62 (1H, m), 4.45 (2H, q, J=7.1 Hz), 3.90 (4H, m), 3.28 (4H, m), 2.28 (3H, s), 1.45 (3H, t, J=7.1 Hz). Mass Spectrum (pos.) m/e: 555.2 (M+1).

Provenance & Evidence