Reference of 15862-37-0 ,Some common heterocyclic compound, 15862-37-0, molecular formula is C5H2Br2N2O2, 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.
Step 1: Methyl 4-(5-bromo-3-nitropyridin-2-yl)-3-fluorobenzoateTo a solution of (2-fluoro-4-(methoxycarbonyl)phenyl)boronic acid (0.5 00 g, 2.53mmol) and 2,5-dibromo-3-nitropyridine (0.7 12 g, 2.53 mmol) in THF (8.42 mL) wasadded aq. tripotassium phosphate (2M, 2.53 ml, 5.05 mmol). The reaction was degassedwith bubbling nitrogen, then PdC12(dppf)-CH2C12 adduct (0.124 g, 0.152 mmol) wasadded and the reaction was heated to 70 C for 2 h. The reaction was cooled, diluted withwater, and extracted 3 times with EtOAc. The combined organics were concentrated.The residue was purified via ISCO silica gel chromatography (40 g column; Hex/EtOAc;0 to 100%) to give methyl 4-(5-bromo-3-nitropyridin-2-yl)-3-fluorobenzoate (0.6 10 g,68%). ?H NMR (400MHz, CDC13) oe 9.01 (d, J2.1 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H), 8.02(dd, J8.0, 1.5 Hz, 1H), 7.84-7.73 (m, 2H), 3.97 (s, 3H); LCMS (M+H) = 355.1; HPLC RT = 1.15 mm. Analytical HPLC Method 1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15862-37-0, its application will become more common.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
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