Chloroacetyl chloride → 2-Chloro-N-(5-fluoro-2-pyridinyl)acetamide

To a solution of 2-amino-5-fluoropyridine (300 mg, 2.60 mmol) in DCM (4.0 mL), DIPEA (1.36 mL, 7.79 mmol) was added, followed by chloracetylchloride (0.23 mL, 2.86 mmol). The resulting dark brown reaction mixture was stirred at rt for 2 h, then quenched with water and diluted with DCM. The org. layer was separated and the aq. layer extracted with DCM (1×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure to obtain 2-chloro-N-(5-fluoropyridin-2-yl)acetamide as a brown oil which was used in the next step without further purification. LC-MS conditions A: tR=0.60 min, [M+H]+=189.31.

1. customquenched with water
2. additiondiluted with DCM
3. customlayer was separated
4. extractionthe aq. layer extracted with DCM (1×)
5. washlayers were washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customthe solvent removed under reduced pressure

ORD record

ord-b4627589437849a580b42d81fcef2675

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303023B2