Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 100367-39-3, name is 4-Bromo-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 100367-39-3
General procedure: 5.1.12 2-[4-({[1-Methyl-4-(2-methylpyridin-4-yl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13a) Under argon gas atmosphere, to the mixture of 12 (200 mg, 0.45 mmol), 4-bromo-2-methylpyridine (156 mg, 0.91 mmol), and Na2CO3 (144 mg, 1.36 mmol) in DMF (2.0 mL) and water (0.87 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (PdCl2(dppf)·CH2Cl2, 22 mg, 0.027 mmol), and the mixture was stirred at 100 C for 1 h. After cooling at room temperature, the mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0-5% MeOH in CHCl3) to give a free from of the title compound, which was dissolved in MeOH and the mixture was treated with 4 M HCl/EtOAc. The precipitate formed was collected by filtration and washed with Et2O to give 13a (91 mg, 42%) as a colorless solid. 5.1.14 2-[4-({[4-(2-Methoxypyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13c) Compound 13c was prepared from 12 and 4-bromo-2-methoxylpyridine in a manner similar to that described for compound 13a, with a yield of 51% as a colorless solid. 1H NMR (DMSO-d6) delta 3.79 (s, 3H), 3.95 (s, 3H), 5.47 (s, 2H), 7.29 (s, 1H), 7.41 (dd, 1H, J = 5.9, 1.3 Hz), 7.71-7.76 (m, 3H), 7.89-7.95 (m, 1H), 8.13 (d, 1H, J = 8.2 Hz), 8.17 (d, 1H, J = 5.9 Hz), 8.28 (d, 2H, J = 8.7 Hz), 8.33 (d, 2H, J = 8.4 Hz), 8.45 (s, 1H), 8.72 (d, 1H, J = 8.6 Hz); MS (ESI) m/z 423 [M+H]+; Anal. Calcd for C26H22N4O2·2.2HCl·3.5H2O: C, 56.10; H, 5.58; N, 10.06; Cl, 12.74. Found: C, 56.33; H, 5.68; N, 9.88; Cl, 12.52.
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Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Shiina, Yasuhiro; Kikuchi, Shigetoshi; Mihara, Takuma; Moriguchi, Hiroyuki; Fushiki, Hiroshi; Murakami, Yoshihiro; Amano, Yasushi; Honbou, Kazuya; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 2; (2015); p. 297 – 313;,
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