Acetyl chloride → N-(6-Bromo-pyridin-2-ylmethyl)acetamide

Temperature

40 °C

To a solution of C-(6-Bromo-pyridin-2-yl)-methylamine (5440 mg, 29.08 mmol) in dichloromethane (100 mL) at room temperature was added triethylamine (5886 mg, 58.17 mmol) and acetyl chloride (2511 mg, 31.99 mmol). The reaction mixture was heated at 40° C. for 3 h and cooled down to room temperature. A solution of sodium hydroxide (1N) was added and the reaction was stirred for 1 h at room temperature. The layers were separated and the organic phase was concentrated under reduced pressure. The crude mixture was dissolved in EtOH (50 mL) and concentrated hydrochloric acid (10 mL) was added. The mixture was stirred for 30 min and benzene was added followed by sodium hydroxide pellets until pH 10 was reached. The phases were separated and the organic layer was washed with an aqueous solution of ammonium chloride and the volatiles were removed in vacuo. The crude material was purified by column chromatography with a gradient of 0 to 5% methanol/dichloromethane to give N-(6-Bromo-pyridin-2-ylmethyl)acetamide as viscous orange oil. MS ES (MH+ 229.1/231.0).

1. temperaturecooled down to room temperature
2. customThe layers were separated
3. concentrationthe organic phase was concentrated under reduced pressure
4. dissolutionThe crude mixture was dissolved in EtOH (50 mL)
5. additionconcentrated hydrochloric acid (10 mL) was added
6. stirringThe mixture was stirred for 30 min
7. additionbenzene was added
8. customThe phases were separated
9. washthe organic layer was washed with an aqueous solution of ammonium chloride
10. customthe volatiles were removed in vacuo
11. customThe crude material was purified by column chromatography with a gradient of 0 to 5% methanol/dichloromethane

ORD record

ord-e29080a9ae5f4d538b9f088b15dbec7d

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803956B2