Triethylamine → 3-chloro-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

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Reaction Steps

524 mg (1.98 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (1-2) are dissolved in 20 ml of acetonitrile, then 414 μl (2.97 mmol) of triethylamine and 317 mg (2.37 mmol) of N-chlorosuccinimide are added at room temperature. After one hour of stirring, a 159 mg (1.19 mmol) of N-chlorosuccinimide are added. After a further hour of stirring, the entire reaction mixture is concentrated under reduced pressure. The residue is taken up in dichloromethane, washed successively twice with 1N aqueous hydrochloric acid, twice with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (2:1) gives 430 mg (72% of theory) of 3-chloro-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one.

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