Sodium Sulfate → HCID 56597563, compound

Participants

Reaction Steps

To a 20 mL microwave vial were sequentially added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (100 mg, 0.267 mmol, 3-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (69.2 mg, 0.294 mmol), PdCl2(dppf)-CH2Cl2 adduct (21.84 mg, 0.027 mmol), (DME) (5 mL), and water (2 mL). The reaction mixture was degassed with nitrogen for 5 min. Sodium bicarbonate (67.4 mg, 0.802 mmol) was added and the contents sealed and irradiated (microwave) at 140° C. The reaction mixture was cooled to room temperature and poured on a silica column (through Na2SO4) and purified by silica gel chromatography (eluent: 5% MeOH/CH2Cl2) which provided the desired product as an off-white solid after preciptation from EtOAc/MeOH. The final product was collected as 0.090 g (76%). LCMS E-S (M+H) 447.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.57 (s., 1H), 9.06 (d, J=1.52 Hz, 1H), 8.92-9.00 (m, 1H), 8.39-8.48 (m, 2H), 8.24 (s, 1H), 8.14 (d, J=1.77 Hz, 1H), 5.91 (s, 1H), 5.30-5.45 (m, 1H), 4.42 (d, J=4.80 Hz, 2H), 3.97 (s, 3H), 2.24 (s, 3H), 2.13 (s, 3H), 1.55 (d, J=6.82 Hz, 6H).

Provenance & Evidence