With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.Computed Properties of C6H4BrN3
To a solution of 2-amino-5-bromonicotinonitrile (1.4 equiv.) in toluene and ethanol (2.5:1) was added N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)-3-(trifluoromethyl)benzamide (1.0 equiv.), Pd(PPh3)4 (0.1 equiv.) and aqueous potassium carbonate (3M, 3.0 equiv.). The reaction was heated in the microwave at 120 C for 40 min. The organic layer was separated and concentrated to dryness under vacuo. The residue was dissolved in DMSO and purified via reverse phase HPLC. The pure fractions were lyophilized to give N-(3-(6-amino-5-cyanopyridin-3-yl)-4-methylphenyl)-3- (trifluoromethyl)benzamide as the TFA salt in 48% yield. 1H NMR (400 MHz, DMSOd6) G 10.45 (s, 1H), 8.30 (s, 1H), 8.25 (d, J=2.0, 1H), 8.23 (d, J=2.0, 1H), 7.97 (d, J=8.0, 1H), 7.95 (d, J=4.0, 1H), 7.79 (t, J=8.0, 1H), 7.72 (dd, J=8.0, 2.0, 1H), 7.61 (d, J=4.0, 1H), 7.30 (d, J=12.0, 1H), 2.23 (s, 3H). LCMS (m/z) (M+H) = 397.1, Rt = 0.91 min.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,709652-82-4, 2-Amino-5-bromonicotinonitrile, and friends who are interested can also refer to it.
Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); A1;,
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