Potassium Carbonate → HCID 90403273, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example A4 (0.676 g, 2.55 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine (1 g, 3.31 mmol), Pd(PPh3)4 (0.147 g, 0.127 mmol) and K2CO3 (1.055 g, 7.64 mmol) in dioxane (8 mL) and water (2 mL) was sparged with Ar, heated at 90° C. overnight, then cooled to RT. The mixture was treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-methyl-4-(4-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)phenyl)piperazine (333 mg, 32%). 1H NMR (400 MHz, DMSO-d6): δ 8.55 (d, J=5.6 Hz, 1H), 8.22 (d, J=8.7 Hz, 1H), 7.95 (d, J=8.8 Hz, 2H), 7.81 (d, J=8.7 Hz, 1H), 7.58 (d, J=2.3 Hz, 1H), 6.98 (d, J=8.8 Hz, 2H), 6.94 (dd, J=5.6, 2.3 Hz, 1H), 3.21 (m, 4H), 2.52 (s, 3H), 2.43 (m, 4H), 2.21 (s, 3H); MS (ESI) m/z: 406.2 (M+H+).

Provenance & Evidence