3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 71254131, compound

Participants

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-(3-cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate were reacted. The product was coupled with 3-pyridineboronic acid pinacol ester by the Suzuki coupling procedure of Example 10 and deprotected by the procedure of Example 225. The mixture was purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 37 mg (19%) of 240 over three steps. ESI MS m/z 382.2 (M+1). 1H NMR (400 MHz, DMSO): 9.41 (s, 1H), 9.23 (s, 1H), 8.68-8.59 (m, 2H), 8.55 (d, J=7.8 Hz, 1H), 7.87 (s, 1H), 7.80 (s, 1H), 7.56-7.50 (m, 1H), 7.43 (s, 1H), 3.26-3.23 (m, 4H), 2.87-2.81 (m, 4H)

Provenance & Evidence