Picolinic acid → N-(2-Bromoethyl)pyridine-2-carboxamide

Picolinic acid (0.99 g) in dichloromethane (30 mL) was treated with triethylamine (1.27 mL) and HATU (3.6 g). The mixture was stirred for 10 minutes then a solution of 2-bromoethylamine hydrobromide (1.5 g) and triethylamine (1.27 mL) in dichloromethane (20 mL) was added. The reaction mixture was stirred for 3h. Water (50 mL) was added and the layers were separated. The organic layer was washed with water (3×50 mL), dried over magnesium sulphate and evaporated to afford the crude product which was purified by silica gel chromatography eluting with 0-100% EtOAc/dichloromethane. The relevant fractions were combined and evaporated, dissolved up in EtOAc (40 mL) and washed with saturated sodium hydrogen carbonate solution, ensuring the aqueous layer remained basic. The organic layer was dried over magnesium sulphate and evaporated to give the sub-titled compound (0.88 g) as a white solid.

1. stirringThe reaction mixture was stirred for 3h
2. customthe layers were separated
3. washThe organic layer was washed with water (3×50 mL)
4. dry with materialdried over magnesium sulphate
5. customevaporated
6. customto afford the crude product which
7. customwas purified by silica gel chromatography
8. washeluting with 0-100% EtOAc/dichloromethane
9. customevaporated
10. dissolutiondissolved up in EtOAc (40 mL)
11. washwashed with saturated sodium hydrogen carbonate solution
12. dry with materialThe organic layer was dried over magnesium sulphate
13. customevaporated

ORD record

ord-b33c8ec9c2bf4e5184a3e9bb02ebd255

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329729B2