Triethylamine → N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamide

To 6-chloropyridin-2-amine (20.0 g, 156 mmol) and triethylamine (23.7 mL, 171 mmol) in 100 mL toluene at 50° C. was added pivaloyl chloride (19.6 mL, 163 mmol) dropwise via syringe. The reaction mixture was allowed to stir, and eventually became a solid mass. 50 mL toluene was added. The reaction mixture was heated overnight, and cooled to ambient temperature. The reaction mixture was quenched with 400 mL 2N aq. HCl, and diluted with 300 mL EtOAc. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated to a solid. The solid was dissolved in a min. volume of hot MTBE (50° C.), and approx. 300 mL hexanes was added with swirling. On standing, crystals form, which were collected by filtration, rinsing with hexanes to give a total of N-(6-chloropyridin-2-yl)pivalamide. MS (ESI) m/z: calculated: 212.1; Observed: 213.2 (M++1).

1. temperatureThe reaction mixture was heated overnight
2. customThe reaction mixture was quenched with 400 mL 2N aq. HCl
3. additiondiluted with 300 mL EtOAc
4. washThe organic layer was washed with water, brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to a solid
8. dissolutionThe solid was dissolved in a min
9. additionvolume of hot MTBE (50° C.), and approx. 300 mL hexanes was added
10. filtrationcrystals form, which were collected by filtration
11. washrinsing with hexanes

ORD record

ord-51ecdc092fff4736a4e9e0d221621825

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842685B2