Related Products of 13273-53-5, 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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
To a solution of the crude (S)-4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide (30 mg, 0.059 mmol) in residual dioxane was added 4-bromo-1-methyl-1H-1,2,3-triazole (14.24 mg, 0.088 mmol), PdCl2(dppf) (42.9 mg, 0.059 mmol), DME (195 mul) and 2 M Na2CO3 (130 mul) at room temperature. The reaction mixture was stirred for 5 h. After water and EtOAc were added, the organic layer was extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude product was purified by prep HPLC. The pure fractions were lyophilized yielding (S)-4-(2-amino-5-(1-methyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide as a TFA salt (25% over 2 steps). LCMS (m/z): 467.3 (MH+), 0.61 min; 1H NMR (400 MHz, CD3OD) delta ppm 8.64 (m, 1H), 8.31 (m, 1H), 8.25 (m, 2H), 8.2 (m, 1H), 7.82 (m, 1H), 7.4 (m, 3H), 7.28 (m, 2H), 7.22 (m, 1H), 5.11 (m, 1H), 4.07 (s, 3H), 3.78 (m, 2H).
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Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics