Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 95897-49-7, name is 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine. A new synthetic method of this compound is introduced below., name: 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine
Into a 100 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of n-BuLi in hexane (2.5 M, 2 mL, 5.0 mmol, 0.54 equiv) and a solution of n-Bu2Mg in heptanes (1.0 M, 4.8 mL, 4.8 mmol, 0.53 equiv). The resulting solution was stirred for 10 min at RT (20 C). This was followed by the dropwise addition of a solution of 7-bromo-2H,3H-[1,4]dioxino[2,3-b]pyridine (2 g, 9.26 mmol, 1.00 equiv) in tetrahydrofuran (16 mL) with stirring at -10 C in 10 min. The resulting mixture was stirred for 1 h at -10 C. The reaction mixture was slowly added to a solution of thionyl chloride (16 mL) at -10 C. The resulting mixture was stirred for 0.5 h at -10 C. The reaction was then quenched by the careful addition of 30 mL of saturated ammonium chloride solution at 0 C. The resulting mixture was extracted with 3×50 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluting with ethyl acetate/petroleum ether (1:3). This provided 1.3 g (60%) of 2H,3H-[1,4]dioxino[2,3-b]pyridine-7-sulfonyl chloride as a white solid. LCMS m/z: calculated for C7H6ClNO4S: 235.64; found: 236 [M+H]+.
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Reference:
Patent; FORMA THERAPEUTICS, INC.; ERICSSON, Anna; GREEN, Neal; GUSTAFSON, Gary; HAN, Bingsong; LANCIA, JR., David R.; MITCHELL, Lorna; RICHARD, David; SHELEKHIN, Tatiana; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; (140 pag.)WO2018/175474; (2018); A1;,
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