Electric Literature 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.
Cyclopropylmethanol (0.247 mL, 3.12 mmol) was dissolved in dry THF (10 mL) and sodium hydride (60% w/w) (125 mg, 3.12 mmol) was added portion-wise, under nitrogen, at rt. After -30 min, 4- bromo-2-chloropyridine (0.173 mL, 1.559 mmol) was added slowly and the reaction was stirred at rt for 5 days. The reaction was diluted with Et20 (30 mL) and washed with water (20 mL). The organic layer was washed with brine, dried using a hydrophobic frit and evaporated to give a yellow oil (0.432g). The residue was loaded in DCM and purified on the Biotage SP4 silica (Si) SNAP 25g column using a 0-20% EtOAc/cyclohexane gradient. Appropriate fractions were combined and evaporated to give a colourless oil (295 mg) This was loaded in cyclohexane and purified by Biotage SP4 SNAP 25g silica using a gradient of 0-10% EtOAc/cyclohexane gradient. Fractions containing product were combined and evaporated under vacuum to give a colourless oil which was dissolved in 1 :1 MeOH:DMSO 1 mL (x3) and purified by MDAP. The solvent was evaporated under vacuum to give a the title compound as a colourless oil (97 mg). LCMS (2 min, Formic Acid): Rt = 1.21 min, MH+ = 228/230.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73583-37-6, 4-Bromo-2-chloropyridine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; BAMBOROUGH, Paul; BIT, Rino, Antonio; BROWN, John, Alexander; CAMPBELL, Matthew; LINDON, Matthew, John; SHIPLEY, Tracy, Jane; THEODOULOU, Natalie, Hope; WELLAWAY, Christopher, Roland; WESTAWAY, Susan, Marie; WO2014/78257; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem