2-Bromo-3-nitropyridine → 7-Bromo-6-azaindole

A solution of 2-Bromo-3-nitropyridine (1 in Scheme 1, 2.0 g, 98%, 9.7 mmol) in dry THF (80 mL) was cooled to −78° C. Excess vinylmagnesium bromide (1.0 M in THF, 40 mL, 40 mmol) was added. The reaction mixture was stirred at −40˜−50° C. for 1 h before it was quenched with saturated NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc (3 times). The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography (EtOAc:n-hexane=1:2) to afford 2 (1.1 g, 60%).

1. customwas quenched with saturated NaHCO3 solution
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with EtOAc (3 times)
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationthe dried solution was filtered
6. concentrationthe filtrate was concentrated
7. customThe residue was purified by flash chromatography (EtOAc:n-hexane=1:2)

ORD record

ord-fb270304bbbf4a7eb9857822f77325c5

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119683B2