Dimethylamine → 2-(5-bromopyridin-3-yl)-N,N-dimethylacetamide

(5-Bromopyridin-3-yl)acetic acid (500 mg, 2.31 mmol) was dissolved in dichloromethane (5 mL), treated with di-iso-propylamine (402.4 μL, 2.31 mmol) and cooled in an ice water bath. Pivaloyl chloride (284.7 μL, 2.31 mmol) was added and the mixture was stirred for 25 minutes. 2 M dimethylamine (1.73 mL, 3.46 mmol) was added and the reaction was stirred 15 h. The mixture was washed with saturated ammonium chloride (1×), saturated sodium bicarbonate (1×), and dried over sodium sulfate to yield 2-(5-bromopyridin-3-yl)-N,N-dimethylacetamide as a brown oil (445 mg, 79%). MS: m/z 562 (M+H+).

1. temperaturecooled in an ice water bath
2. stirringthe reaction was stirred 15 h
3. washThe mixture was washed with saturated ammonium chloride (1×), saturated sodium bicarbonate (1×)
4. dry with materialdried over sodium sulfate

ORD record

ord-f3550df0ed4b4b4e8dd1d1801f52bc51

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242280B2