Water → HCID 71543548, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (90 mg, 0.23 mmol) and 3-pyridinylboronic acid (42.8 mg, 0.35 mmol) in dioxane/water (3:1 mL). PdCl2(dppf)-CH2Cl2 adduct (9.47 mg, 0.012 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium carbonate (58.5 mg, 0.7 mmol) was added, the vessel was sealed, and the insoluble mixture was heated in a microwave to 110° C. for 20 min. Upon cooling, water was added and solids that precipitated were filtered, dissolved in DCM and purified by SiO2 chromatography (eluent: gradient 0 to 80:20:2 DCM/MeOH/NH4OH). The product containing fractions were evaporated and suspended in EtOH/EtOAc (1:1). The contents were sonicated, solids that precipitated were filtered, washed with hexanes and dried to afford the title compound as a white solid (78 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (br. s., 1 H) 9.39 (d, J=1.52 Hz, 1 H) 8.76 (t, J=5.05 Hz, 1 H) 8.69 (dd, J=4.67, 1.64 Hz, 1 H) 8.57 (dt, J=8.27, 1.80 Hz, 1 H) 7.78 (s, 1 H) 7.57 (dd, J=8.08, 5.56 Hz, 1 H) 5.89 (s, 1 H) 5.28 (quin, J=6.69 Hz, 1 H) 4.41 (s, 1 H) 4.39 (s, 1 H) 2.46 (s, 3 H) 2.25 (s, 3 H) 2.12 (s, 3 H) 1.52 (s, 3 H) 1.51 (s, 3 H); LC-MS (ES) m/z=431.1 [M+H]+.

Provenance & Evidence