Reference of 73583-37-6 ,Some common heterocyclic compound, 73583-37-6, molecular formula is C5H3BrClN, 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.
To a stirring solution of 4-bromo-2-chloropyridine (2.0 g, 10.39 mmol) in diethyl ether (30 mL) at -70 C under nitrogen was added n- butyllithium, 2.5 M solution in hexanes (4.57 mL, 11.43 mmol) at a rate not to exceed -65 C. A white precipitate had formed. After 5 min a solution of cyclopropyl methyl ketone (Lancaster Synthesis, Ltd., 1.030 mL, 10.39 mmol) in diethyl ether (5 mL) was added to the suspension. After 5 min the cooling bath was removed and warmed to -15 C. The suspension was then quenched with saturated NH4C1 (15 mL) and EtOAc (20 mL) added. The separated organic was then dried over MgSC^, concentrated under reduced pressure, then purified by silica gel chromatography (80 g) eluting products with 10 to 30% gradient of EtO Ac/Hex to afford l-(2-chloro-4-pyridinyl)-l-cyclopropylethanol (1.35 g, 6.83 mmol, 65.7 % yield) as amber oil (mixture of 2 enantiomers).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-37-6, its application will become more common.
Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
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