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 funnel. 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-2248edbebf3d43fdafeab039658ef756

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700636B2