39856-56-9

13534-97-9

74-88-4

39856-56-9

5-Amino-2-bromopyridine (300 mg, 1.73 mmol) was dissolved in tetrahydrofuran (30 mL) under nitrogen protection and cooled to -78 °C. A tetrahydrofuran solution of 1 M bis(trimethylmethylsilyl)lithium amide (3.46 mL, 3.46 mmol) was slowly added to this solution over 6 min. After maintaining -78 °C and stirring for 30 min, iodomethane (566 mg, 3.99 mmol) was added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (50 mL). The reaction mixture was extracted with ethyl acetate (3 x 50 mL) and the organic phases were combined. The organic phase was washed sequentially with brine (2 x 50 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with the eluent being a petroleum ether solution of 1-10% ethyl acetate to give 6-bromo-N,N-dimethylpyridin-3-amine as a light yellow solid. Mass spectrum (ESI, m/z): 201.0,203.0 [M + 1]+.