Electric Literature of 609-12-1, These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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.
Under an atmosphere of nitrogen, an ice-cooled solution of 6-methoxyisoindolin-1-one (commercially available from for example Astatech) (105 mg, 0.64 mmol) in DMF (2.5 mL) was treated with sodium hydride (60% w/w in mineral oil) (31 mg, 0.77 mmol) and the mixture was allowed to warm to ambient temperature. The mixture was then treated with ethyl 2-bromo-3-methylbutanoate (commercially available from for example Alfa Aesar) (135 mg, 0.64 mmol) and the mixture was stirred for 18 hours then cautiously treated with saturated aqueous ammonium chloride (20 mL). The product was extracted with ethyl acetate (2*25 mL) and the combined organic phase was washed with water (20 mL), brine (20 mL), filtered through a hydrophobic fit and evaporated to dryness. the product was purified by flash chromatography (20 g silica cartridge) using a gradient elution from 0 to 50% ethyl acetate in cyclohexane to afford the title compound (40 mg, 21% yield). LCMS RT=1.03 min, ES+ve m/z 292 [M+H]+
The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Crews, Craig M.; Buckley, Dennis; Ciulli, Alessio; Jorgensen, William; Gareiss, Peter C.; Van Molle, Inge; Gustafson, Jeffrey; Tae, Hyun-Seop; Michel, Julien; Hoyer, Dentin Wade; Roth, Anke G.; Harling, John David; Smith, Ian Edward David; Miah, Afjal Hussain; Campos, Sebastien Andre; Le, Joelle; US2014/356322; (2014); A1;,
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