Sodium Carbonate → N-((4-bromopyridin-2-yl)methyl)formamide

Temperature

100 °C

To a 500-mL round-bottom flask, was placed (4-bromopyridin-2-yl)methanamine (compound 39.1, 8.0 g, crude) and formic acid (200 mL). The solution was stirred for 2 h at 100° C., then cooled and the pH was adjusted to 7 by careful and slow addition of aqueous sodium carbonate (sat.). The aqueous phase was extracted with ethyl acetate (3×200 mL) and the combined organic layers were washed with brine (3×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate as the eluent to yield the title compound as a yellow oil (8.0 g, 90% pure, 65% yield over 2 steps).

1. customTo a 500-mL round-bottom flask, was placed
2. temperaturecooled
3. extractionThe aqueous phase was extracted with ethyl acetate (3×200 mL)
4. washthe combined organic layers were washed with brine (3×30 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography with ethyl acetate as the eluent

ORD record

ord-4e8ffa804d234f16bd458b01b787537e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2