Application of 60166-43-0, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
1,4-Dimethyl-1H-1,2,3-triazole (0.057 g, 0.588 mmol), potassium acetate (0.192 g,1.960 mmol), PdOAc2 (8.80 mg, 0.039 mmol) and di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (cataCXium A) (0.028 g, 0.078 mmol) were suspended in 2- methylbutan-2-ol (2.57 ml, 23.51 mmol) under nitrogen. The reaction mixture was purged with nitrogen for 5 mm and then ()-5-(5-bromo-1-(4,4-difluorocyclohexyl)-1H- benzo[d]imidazol-2-yl)-1-(3,4-difluoro phenyl)pyrrolidin-2-one (0.2 g, 0.392 mmol) was added. The green suspension was heated to 100C for 24h. The reaction was cooledto RT and partitioned between EtOAc (40 mL) and water (30 ml). The organic phase was separated, washed with brine (25 ml) and then dried over MgSO4, filtered and concentrated in vacuo to afford a yellow oil.The crude product was purified by chromatography on silica gel (24 g column, 0-5% MeOH/DCM) to afford (S)-5-(1-(4,4- difluorocyclohexyl)-5 -(1 ,4-dimethyl- 1 H- 1,2,3 -triazol-5 -yl)- 1 H-benzo[d] imidazol-2-yl)-1-(3,4-difluorophenyl)pyrrolidin-2-one (69.5 mg, 33%) as beige solid; Rt 2.02 mm(method 1), mlz 527 (M+H)+ (ES+); 1H NIVIR (d6-DMSO) : 7.86 (ddd, J = 13.3, 7.4,2.7 Hz, 1H), 7.77 (d, J = 1.5 Hz, 1H), 7.67 (d, J = 8.5 Hz, 1H), 7.38 (q, J = 10.6, 9.2 Hz,1H), 7.32 (dd, J = 8.5, 1.7 Hz, 1H), 7.22 – 7.14 (m, 1H), 6.12 – 6.06 (m, 1H), 4.88 – 4.77(m, 1H), 3.90 (s, 3H), 2.81 -2.61 (m, 2H), 2.61 -2.42 (m, 3H), 2.31 -2.21 (m, 3H),2.19 (s, 3H), 2.17- 1.93 (m, 4H).
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Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; TADDEI, David Michel Adrien; SHANNON, Jonathan; PAOLETTA, Silvia; QIN, Ting; HARBOTTLE, Gareth; (95 pag.)WO2018/73587; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics