Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,4-Dimethyl-1H-1,2,3-triazole
(S)-3-bromo-7-(methylsulfonyl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrrolo[2,3-b:4,5-b’]dipyridine (30 mg, 0.060 mmol) was dissolved in 1.5 mL of NMP and added l,4-dimethyl-lH-l,2,3-triazole (9.3 mg, 0.096 mmol). Tetramethylammonium acetate (12.0 mg, 0.090 mmol) and bis(triphenylphosphine)palladium(II) chloride (3.0 mg, 4.20 muetaiotaomicron) were added. Argon was bubbled through the mixture while sonicating for 5 min. The vial was capped and heated at 100 C for 33 h, then cooled and the contents of the vial were filtered. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 19 x 200 mm, 5-muiotatauiota particles;Mobile Phase A: 5:95 methanol: water with 10-mM NH4OAC; Mobile Phase B: 95:5 methanol: water with 10-mM ammoniumacetate; Gradient: 45-85% B over 15 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 2.8 mg (9%), and its estimated purity by LCMS analysis was 100%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH CI 8, 2.0 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM Nl UOAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. RT = 2.27, M+H = 517. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM NEUOAc; Mobile Phase B: 95:5 methanol: water with 10 mM NlrUOAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. RT = 2.27, M+H = 517. NMR (500MHz, DMSO- de) delta 8.96 (d, J=8.1 Hz, 1H), 8.76 (s, 2H), 8.05 (d, J=8.1 Hz, 1H), 7.83 (d, J=7.7 Hz, 2H), 7.33 (t, J=7.5 Hz, 2H), 7.26 (t, J=7.3 Hz, 1H), 5.93 (br. s., 1H), 4.07 (s, 3H), 3.95 – 3.83 (m, 1H), 3.82 – 3.60 (m, 2H), 3.47 – 3.36 (m, 1H), 3.31 – 3.19 (m, 1H), 2.34 (s, 3H), 1.59 – 1.49 (m, 1H), 1.49 – 1.38 (m, 1H), 1.38 – 1.22 (m, 1H), 1.16 (d, J=12.1 Hz, 1H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
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