5-Bromo-2-chloro-N-methoxy-N-methylnicotinamide → 1-(5-Bromo-2-chloropyridin-3-yl)ethanone

Temperature

-78 °C

Starting material 5-bromo-2-chloro-N-methoxy-N-methylnicotinamide (5.0 g, 17.89 mmol) was charged into a 250 ml round bottom flask and the flask was chilled to −78° C. Methyl magnesium bromide 96.5 ml, 19.68 mmol) in 5 ml THF was added dropwise via addition finnel. The resulting mixture was allowed to stir for 3 hours at −78° C. After removing the THF solvent via rotatory evaporation under reduced pressure, the reaction mixture was partitioned between ethylacetate and saturated aqueous sodium bicarbonate. After removing the ethylacetate, the resulting crude product was subject to a silica gel column with 20% ethylacetate in hexane. The resulting product (2.28 g, y=54.3%) was used for the following step.

1. additionwas charged into a 250 ml round bottom flask
2. customAfter removing the THF solvent
3. customvia rotatory evaporation under reduced pressure
4. customthe reaction mixture was partitioned between ethylacetate and saturated aqueous sodium bicarbonate
5. customAfter removing the ethylacetate

ORD record

ord-5c7668561ae54361bbfd5c29d9f1c39a

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354944B2