Application of 92276-38-5, 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. 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine. A new synthetic method of this compound is introduced below.
General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, and friends who are interested can also refer to it.
Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
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