Reference of 262587-05-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 262587-05-3 as follows.
A nitrogen-purged mixture of tris(dibenzylideneacetone)dipalladium(0) (0.0193 g, 0.021 mmol), and di-tert-butyl(2′,4′,6′-triisopropyl-3,4,5,6-tetramethyl-[1,1′-biphenyl]-2-yl)phosphine (0.0251 g, 0.052 mmol) in toluene (2.2 mL) was stirred for 20 minutes and then added to an nitrogen-purged mixture of methyl 3-cyclobutyl-4-[4-(morpholin-4-yl)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-6-carboxylate (0.1760 g, 0.441 mmol, E509), 1-bromo-3-(difluoromethoxy)benzene (0.1179 g, 0.529 mmol), and Cs2CO3 (0.2143 g, 0.658 mmol). The mixture was heated to 70 C overnight, diluted with water, extracted with DCM (3 x 8 mL), dried (Na2SO4), and concentrated. The residue was chromatographed on silica (30-60% EtOAc/DCM to 4% MeOH/DCM) and re-chromatographed (2.5-4% zPrOH/DCM) to give the titled compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.28 – 8.16 (m, 2H), 7.58 (t, J = 8.2 Hz, 1H), 7.51 – 7.03 (m, 3H), 3.95 (dq, J = 18.1, 9.8, 8.5 Hz, 1H), 3.88 (s, 3H), 3.63 – 3.48 (m, 6H), 2.91 (t, J = 11.9 Hz, 2H), 2.53 – 2.48 (m, 4H), 2.46 – 2.28 (m, 2H), 2.12 – 1.88 (m, 4H), 1.63 (td, J = 13.1, 12.6, 6.4 Hz, 2H).
According to the analysis of related databases, 262587-05-3, the application of this compound in the production field has become more and more popular.