Electric Literature of 75291-85-9 , The common heterocyclic compound, 75291-85-9, name is 5-Bromo-2-chloronicotinamide, molecular formula is C6H4BrClN2O, 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.
General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7%).; The title compound was prepared using 5-bromo-2-chloronicotinamide (1.50 g, 6.37 mmol), tert-butyl piperazine 1-carboxylate (1.19 g, 6.37 mmol) and potassium carbonate (3.52 g, 25.48 mmol) in acetonitrile (20 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (2.25 g, 91.8%).MS (ESI, pos. ion) m/z: 385.2 [M+H] and?H NMR (400 IVIFIz, DMSO-d6): (ppm) 8.31 (d, J= 2.4 Hz, 1H), 7.95 (s, 1H), 7.82 (d, J= 2.0 Hz, 1H), 7.63 (s, 1H), 3.42 (d, J= 4.8 Hz, 4H), 3.27 (d, J= 4.8 Hz, 4H), 1.41 (s, 9H).
The synthetic route of 75291-85-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; LIANG, Haiping; YI, Chao; ZHANG, Ji; (94 pag.)WO2016/192657; (2016); A1;,
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