5-Bromo-2-methyl-3-nitropyridine → 4-bromo-7-methyl-1H-pyrrolo[2,3-c]pyridine

Temperature

-50 °C

5-Bromo-2-methyl-3-nitropyridine (217 mg, 1 mmol) was dissolved in THF (10 mL) and the solution was cooled to −50° C. under argon. Vinylmagnesium bromide (3 mL, 1M in THF) was added immediately in one portion, resulting in a bright orange solution. The orange solution was stirred at −40° C. for 30 min and the reaction was quenched by the addition of NH4Cl (10 mL of saturated. aqueous solution). The mixture was diluted with water and extracted with EtOAc (2×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. The crude material was purified by chromatography on silica (Si—PPC) using EtOAc in cyclohexane (20-80%) as eluent to give the product as a pale yellow crystalline solid (63 mg, 30%). 1H NMR (CDCl3) 8.23 (s, 1H), 7.41-7.45 (m, 1H), 6.62-6.65 (m, 1H), 2.73 (s, 3H)

1. customresulting in a bright orange solution
2. customthe reaction was quenched by the addition of NH4Cl (10 mL of saturated. aqueous solution)
3. additionThe mixture was diluted with water
4. extractionextracted with EtOAc (2×10 mL)
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. concentrationconcentrated
7. customThe crude material was purified by chromatography on silica (Si—PPC)

ORD record

ord-79772ce624bf4ad6a9bfc530e13bff06

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2