Methylamine → 6-Bromo-N-methylnicotinamide

N,N′-Carbonyldiimidazole (480 mg, 2.96 mmol) was added to a solution of 6-bromonicotinic acid (480 mg, 2.96 mmol) in dimethylsulfoxide (2 mL) and the mixture was stirred for 24 hours. Methylamine (2M in THF, 6 mL, 12 mmol) was then added and the mixture was stirred for a further 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was diluted with water (25 mL) and extracted with dichloromethane (3×10 mL). The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to afford the title compound as a colourless solid in 59% yield, 300 mg.

1. stirringthe mixture was stirred for a further 18 hours
2. customThe reaction mixture was evaporated under reduced pressure
3. additionthe residue was diluted with water (25 mL)
4. extractionextracted with dichloromethane (3×10 mL)
5. dry with materialThe combined organic extracts were dried over sodium sulphate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography on silica gel
8. washeluting with ethyl acetate

ORD record

ord-3ee5aee2e7134269bf4a4d3d11224d05

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557121B2