Dimethylformamide → 2-Chloro-5-fluoropyridine-3-carboxamide

To a solution of 2-chloro-5-fluoronicotinic acid 6 (50 g, 285 mmol) and DMF (2 mL, 28 mmol) in DCM (400 mL) at 0° C. was added oxalyl chloride (64 mL, 741 mmol) dropwise. The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The resulting yellow liquid was dissolved in 1,4-dioxane (600 mL), cooled at 0° C. and NH3(g) was bubbled through the solution for 30 minutes. The mixture was stirred at room temperature overnight. The resulting mixture was filtered and the filtrate was concentrated to give compound 3 (44 g, 89%) as a beige solid. 1H NMR (DMSO-d6, 300 MHz): δ 7.84 (s, 1H), 7.96 (dd, 1H), 8.09 (s, 1H), 8.49 (d, 1H).

1. concentrationconcentrated in vacuo
2. dissolutionThe resulting yellow liquid was dissolved in 1,4-dioxane (600 mL)
3. temperaturecooled at 0° C.
4. customNH3(g) was bubbled through the solution for 30 minutes
5. stirringThe mixture was stirred at room temperature overnight
6. filtrationThe resulting mixture was filtered
7. concentrationthe filtrate was concentrated

ORD record

ord-088ec2e052b045c28853a81cc305b4fa

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242272B2