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

Participants

Reaction Conditions

Reaction Steps

Example 6 was prepared according to the general procedure of Example 1, except that the reaction mixture was heated at 105° C. for 2.25 h and using the following materials: Intermediate 5A (38.0 mg, 0.148 mmol), 3-iodo-4-methoxypyridine (86.2 mg, 0.367 mmol), sodium carbonate (56.1 mg, 0.529 mmol), degassed EtOH:DME:H2O (1.2:2.5:1.0 ratio) (1.5 mL) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol). Example 6 was isolated as an off white solid (14.9 mg, 31.1%). Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 10% Solvent B to 95% Solvent B over 12 min, ret. T=8.6 min. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.75 (1 H, d, J=4.88 Hz), 8.64 (1 H, d, J=5.80 Hz), 8.59 (1 H, s), 8.27-8.36 (3 H, m), 7.42-7.51 (3 H, m), 7.35 (1 H, d, J=6.10 Hz), 3.93 (3 H, s). LC/MS (Condition B): ret. T=2.84 min, (M+H)+ 321.05. Analytical HPLC: (Condition A): >99%, ret. T=22.96 min, (Condition B): >99%, ret. T=23.17 min, (Condition C): >99%, ret. T=9.33 min, (Condition D): >99%, ret. T=9.91 min.

Provenance & Evidence