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. 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3BrClN
Step 2: N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane- 1 ,2-diamine [00252] A mixture of 4-bromo-3-chloropyridine (0.171 g, 0.886 mmol), N1-(2-aminoethyl)- N2-(7-chloroquinolin-4-yl)-N1-methylethane-l,2-diamine (0.247 g, 0.886 mmol), Pd(OAc)2 (22 mg), BINAP (0.12 g), and K3P04 (1.0 g) in 1,4-dioxane (8.9 mL) was degassed with argon for 5 min and then stirred at 100 C for 16.5 h in a sealed tube. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated in vacuo. Purification by silica gel chromatography using CH2Cl2/CH3OH/NH4OH (270:9: 1, and 180:9: 1) afforded N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane-l,2-diamine (0.276 g, 80%) as a pale-yellow oil, and further lyophilization with CH3CN/H20 gave an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 2.32 (s, 3H); 2.66 (t, J = 6.3, 2H); 2.72 (t, J = 6.6, 2H); 3.26 (q, J = 5.7, 2H); 3.40 (q, J = 6.0, 2H); 6.04 (t, J = 5.0, 1H); 6.50 (d, J = 5.4, 1H); 6.64 (d, J = 5.7, 1H); 7.24 (t, J = 4.8, 1H); 7.43 (dd, J = 2.1, 9.0, 1H); 7.78 (d, J = 2.1, 1H); 8.02 (d, J = 5.7, lH); 8.11 (s, 1H); 8.20 (d, J = 9.3, 1H); 8.38 (d, J = 5.4, 1H). Mass spectrum (ESI) m/e = 390.1 (M+l).
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Reference:
Patent; PRESAGE BIOSCIENCES, INC.; DECKWERTH, Thomas; KLEINMAN, Edward; RUAN, Fuqiang; BAKER, William; KLINGHOFFER, Richard; (126 pag.)WO2016/196393; (2016); A2;,
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