Electric Literature of 151049-87-5, 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 151049-87-5 as follows.
dihydroquinolin- I (211)-yl)-N-methyl- I -(tetrahydro-2H-pyran-4-yI)-6,7-dihydro- I Hpyrazolo[4,3-c}pyridine-5(4H)-carboxamide (Intermediate S. 100 mg, 0.2 mmol) in THF (2.5 mL) and water (0.5 mL) was added chloro(2-dicyclohexylphosphino-2?,4,6?-tri-i-propy1-i,1?-biphenyl)(2?-amino-1,1?-biphenyl-2-yl) palladium (II) (16 mg, 0.02 mmol), 2- (dicyclohexylphosphino)-2?,4?,6?-triisopropylbiphenyl (9 mg, 0.02 mmol), 3 -bromo- 1-methyl- pyrazole (48 mg, 0.3 mmol) and Na2CO3 (42 mg, 0.4 mmol). The reaction was heated to 60C for 16 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was concentrated in vacuo. DCM (50 mL) was added and the mixture was washedwith water (30 mL x 3) and brine (30 mL). The organic layer was dried over anhydrousNa2SO4, filtered and concentrated in vacuo. The crude residue was purified by reverse phasechromatography (acetonitrile 40-70% / 0.05% NH4OH in water) to give the title compound(11 mg, 11%) as a white solid. 111 NMR (400 MHz, DM80-cl6) 6 7.73 (d, Jr 2.0 Hz, IH),7.44 (t,J 55.6 Hz, IH), 7.32 (s, lH), 6.86 (s, 111), 6.55 (d,Jr 4.0 Hz, IH), 6.46 (s, 1H),4.33 -4.23 (m, IH), 4.02 (s, 211), 3.95 – 3.93 (m, 211), 3.86 (s, 311), 3.61 – 3.58 (m, 414), 3.48-3.42 (m, 211), 2.89-2.71 (m, 4H), 2.53 (d,J= 4,4 Hz, 3H), 2.01 – 1.93 (m, 4H), 1.82- 1.80 (m, 211). LCMS M/Z (M+H) 526.
According to the analysis of related databases, 151049-87-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
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