Potassium Carbonate → HCID 90403273, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example A6 (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), K2CO3 (1.055 g, 7.64 mmol) and Pd(PPh3)4 (0.147 g, 0.127 mmol) in dioxane (8 mL) was sparged with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (4×) 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, 1 H), 8.22 (d, J=8.7 Hz, 1 H), 7.95 (d, J=8.8 Hz, 2 H), 7.81 (d, J=8.7 Hz, 1 H), 7.58 (d, J=2.3 Hz, 1 H), 6.98 (d, J=8.8 Hz, 2 H), 6.94 (dd, J=5.6, 2.3 Hz, 1 H), 3.24-3.18 (m, 4 H), 2.52 (s, 3 H), 2.45-2.41 (m, 4 H), 2.21 (s, 3H); MS (ESI) m/z: 406.2 (M+H+).

Provenance & Evidence