Dichloromethane → Methyl 3-(1-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)isonicotinate

Participants

Reaction Steps

Example 12 was prepared according to the general procedure of Example 1, except that the reaction mixture was heated at 105° C. for 1 h in a mixture of NMP (1.0 mL) and water (50 μL) and using the following materials: Intermediate 5A (49.4 mg, 0.192 mmol), 3-bromopyridine-4-carboxylic acid methyl ester (0.035 mL, 0.268 mmol), potassium carbonate (93 mg, 0.671 mmol), and PdCl2(dppf).CH2Cl2 (9 mg, 0.012 mmol). Example 12 was isolated as a tan solid (14.2 mg, 19.8%). Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 30% Solvent B to 100% Solvent B over 12 min, ret. T=10.7 min. LC/MS (Condition B): ret. T=3.6 min, (M+H)+ 349.14. Analytical HPLC: (Condition A): >90%, ret. T=22.18 min, (Condition B): >95%, ret. T=22.85 min, (Condition C): >95%, ret. T=17.14 min, (Condition D): >95%, ret. T=13.96 min.

Provenance & Evidence