Thionyl Chloride → 5-Bromo-N-methylpyridine-2-carboxamide

5-Bromo-pyridine-2-carboxylic acid (2.59 g, 12.8 mmol) and thionylchloride (2.79 ml) were heated at reflux in toluene (25 ml) for 16 hours. Excess reagents were removed in vacuo and the residue was diluted in dichloromethane (50 ml). A mixture of methyl amine hydrochloride (2.60 g, 38.5 mmol) and DIPEA (6.7 ml, 38.5 mmol) in dichloromethane (10 ml) was added dropwise to the stirred solution and the resulting mixture was maintained at room temperature for 5 hours. The solution was washed with saturated aqueous NaHCO3 (25 ml), dried (MgSO4), filtered and concentrated in vacuo. The resulting brown solid was recrystallised (Heptane/EtOAc) to provide the title compound as off-white needles (1.74 g, 63%).

1. customExcess reagents were removed in vacuo
2. additionthe residue was diluted in dichloromethane (50 ml)
3. additionwas added dropwise to the stirred solution
4. washThe solution was washed with saturated aqueous NaHCO3 (25 ml)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting brown solid was recrystallised (Heptane/EtOAc)

ORD record

ord-10ba07166e784d11827685d2f642f38e

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691804B2