Application of 60166-43-0, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, molecular formula is C4H7N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
(R)-l-(7-Chloro-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrrolo[2,3- b:4,5-b’]dipyridin-3-yl)ethanone (30.0 mg, 0.071 mmol), l,4-dimethyl-lH-l,2,3-triazole (10.4 mg, 0.107 mmol), tetramethylammonium acetate (11.4 mg, 0.086 mmol), and PdCl2(PPh3)2 (5.0 mg, 7.1 muetaiotaomicron) were weighed into a 20 mL scintillation vial. DMF (2 mL) was added and the air replaced with nitrogen. The reaction mixture was stirred at 100 C ovemight. The reaction was cooled to room temperature, diluted with EtOAc, and washed twice with brine. The organic layer was dried over MgSC>4 and concentrated. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19 x 200 mm, 5-mupiiota particles; Mobile Phase A: 5:95 methanol: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanol: water with 10- mM ammonium acetate; Gradient: 50-90% B over 20 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 84%. LC/MS [M+H]+ = 481 NMR (500MHz, DMSO-de) delta 9.13 (s, 1H), 8.84 (d, J=8.1 Hz, 2H), 7.72 (d, J=8.1 Hz, 3H), 7.33 – 7.28 (m, 2H), 7.25 – 7.21 (m, 1H), 6.04 (br. s., 1H), 4.34 (s, 3H), 3.89 (d, J=10.3 Hz, 1H), 3.72 (d, J=9.2 Hz, 1H), 3.58 (br. s., 1H), 3.51 (s, 3H), 3.46 – 3.39 (m, 1H), 3.25 – 3.15 (m, 1H), 2.78 (s, 3H), 1.59 (br. s., 1H), 1.51 (d, J=8.8 Hz, 1H), 1.31 (d, J=10.3 Hz, 1H), 1.07 (d, J=14.3 Hz, 1H).
Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1,4-Dimethyl-1H-1,2,3-triazole.
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,
Triazoles – an overview | ScienceDirect Topics