3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → tert-Butyl 4-(4-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

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Reaction Steps

Following the Suzuki coupling procedure of Example 159, 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate were reacted and the product was consequently reacted by the Suzuki coupling procedure of Example 10 with 3-pyridineboronic acid pinacol ester. The product mixture was purified via silica gel chromatography using a gradient of methanol in DCM to afford 230 mg (75%) of tert-Butyl 4-(4-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate over two steps. ESI MS m/z 530.2 (M+1).

Provenance & Evidence