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 337536-15-9 as follows. SDS of cas: 337536-15-9
EXAMPLE 854-(6-Amino-5-((R)-1-(5-fluoro-2-(2H-1 ,2,3-triazol-2-yl)phenyl)ethoxy)pyridin-3- yl)isoindolin-1-oneA mixture of preparation 45 (100 mg, 0.264 mmol), 4,4,5,5,4′,4,,5′,5,-Octamethyl- [2,2′]bi[[1 ,3,2]dioxaborolanyl] (1 14 mg, 1.7 eq), and potassium acetate (90.7 mg, 3.5 eq) in DMSO (1.0 mL) was deoxygenated with N2 bubbler for 30 minutes before addition of the Pd(dppf)CI2 (9.5 mg, 0.05 eq). The mixture was then heated in 80C oil bath for 3 hr. LCMS indicated disappearance of starting bromide. To the crude boronate mixture was added 4-bromoisoindolin-1-one (84 mg, 1.5 eq), CsF (120 mg, 3.5 eq) and MeOH (2 ml_). The mixture was thoroughly degassed and Pd(dppf)Cl2 (9.5 mg, 0.05 eq) was added. The mixture was heated in the microwave at 120 C for 1 hr. LCMS showed the desired product mass. Mixture was filtered and purified with a reverse phasepreparative HPLC under acidic condition to give the title compound as an amorphous white solid (57.8 mg, 50.9%).1H NMR (600 MHz, DMSO-d6) delta ppm 1.59 (d, J=6.14 Hz, 3 H), 4.07 – 4.21 (m, 1 H), 4.23 – 4.34 (m, 1 H), 5.56 (q, J=6.06 Hz, 1 H), 6.19 (s, 2 H), 6.77 (s, 1 H), 7.34 (td, J=8.26, 2.94 Hz, 1 H), 7.41 (d, J=7.42 Hz, 1 H), 7.51 (t, J=7.55 Hz, 1 H), 7.57 (s, 1 H), 7.63 – 7.67 (m, 1 H), 7.70 – 7.72 (m, 1 H), 7.72 (d, J=1.28 Hz, 2 H), 8.20 (s, 1 H), 8.64 (s, 1 H).
According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
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