2-Chloro-3-nitropyridine → 7-Chloro-1H-pyrrolo[2,3-c]pyridine

Temperature

-20 °C

To a solution of 2-chloro-3-nitropyridine (5 g, 31.5 mmol)) in THF (200 mL) at −78° C., was added vinylmagnesium bromide (100 mL, 1.0M in THF) The reaction mixture was stirred at −20° C. for 8 hours, quenched with NH4Cl solution (20%, 150 mL), extracted with EtOAc, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography, eluent EtOAc/hexane (1:5), to afford the title compound 259 (1.23 g, 26% yield) as a white solid [Z. Zhang, et al., J. Org. Chem., 2002, 67, 2345-23471]. MS (m/z): 153.1 (M+H) (found).

1. customquenched with NH4Cl solution (20%, 150 mL)
2. extractionextracted with EtOAc
3. dry with materialdried over anhydrous Na2SO4
4. concentrationconcentrated
5. customThe residue was purified by flash chromatography, eluent EtOAc/hexane (1:5)

ORD record

ord-4006f3a9c0824baf9051a6d6f229d75a

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772247B2