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

To a solution of 2-chloro-5-fluoronicotinic acid 6a (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 3a (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-a7bee5af7b314608b20e437273f150bb

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426425B2