Sodium Carbonate → 4-(4-chloropyridin-3-yl)-1-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

Example 10 was prepared according to the general procedure of Example 1, except that the reaction mixture was heated at 105° C. for 2 h, and using the following materials: Intermediate 5A (40 mg, 0.156 mmol), 3-bromo-4-chloropyridine (53.6 mg, 0.279 mmol), sodium carbonate (61.3 mg, 0.578 mmol), degassed EtOH:DME:H2O (1.2:2.5:1.0 ratio) (1.5 mL) and tetrakis(triphenylphosphine)palladium(0) (25.3 mg, 0.022 mmol). Example 10 was isolated as an off-white solid (5.7 mg, 11%). Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 35% Solvent B to 100% Solvent B over 12 min, ret. T=11.8 min. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.78-8.86 (2 H, m), 8.74 (1 H, d, J=5.19 Hz), 8.37 (1 H, s), 8.26-8.34 (2 H, m), 7.86 (1 H, d, J=5.19 Hz), 7.43-7.55 (3 H, m). LC/MS (Condition B): ret. T=3.8 min, (M+H)+ 325.00, 326.98. Analytical HPLC: (Condition A): >98%, ret. T=24.69 min, (Condition B): >98%, ret. T=24.45 min, (Condition C): >98%, ret. T=18.88 min, (Condition D): >98%, ret. T=15.00 min.

Provenance & Evidence