Synthesis of 3,6-diaryl-1H-pyrazolo[3,4-b]pyridines via one-pot sequential Suzuki-Miyaura couplingElectronic supplementary information (ESI) available: Spectroscopic data for all compounds. CCDC 1828970 and 1817412. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ra07104g

A practical synthesis of diarylpyrazolo[3,4- b ]pyridine derivatives by a combination of chemoselective Suzuki-Miyaura cross-coupling reactions was developed. The sequential arylation strategy can be performed in a one-pot manner without much loss of efficiency when compared to the corresponding stepwise synthesis. These conditions are applicable to the coupling of a wide variety of aryl and heteroaryl-boronic acids with pyrazolo[3,4- b ]pyridines with high selectivity of the C3 over the C6 position, thus enabling the rapid construction of a diverse array of medicinally important diarylpyrazolo[3,4- b ]pyridines. An efficient method to produce diarylpyrazolo[3,4- b ]pyridines derivatives via combination of chemoselective Suzuki-Miyaura cross-coupling reactions has been developed.