N-Methoxy-N-methylacetamide → 1-(6-Chloropyridin-3-yl)ethan-1-one

Temperature

0 °C

A round bottomed flask was charged with 5-bromo-2-chloropyridine (5.30 g, 27.6 mmol) in THF under N2 and cooled at 0° C. A solution of 1 M iso-propylmagnesiumchloride-lithium chloride complex in THF (40 mL) was added drop wise over 15 min. After 70 min N-methoxy-N-methylacetamide (4.1 mL, 38 mmol) was added drop wise. After stirring for 5 min at 0° C. the cooling bath was removed. The mixture was left stirring overnight and was then quenched by the addition of 100 mL saturated aqueous NH4Cl solution. The mixture was extracted with 3×100 mL EtOAc. The combined organic layers were washed with water followed by brine and dried over MgSO4. Evaporation of the volatiles at 80° C., 10 mbar for 1 h gave the title compound (3.596 g, 84) sufficiently pure for the next step.

1. customwas removed
2. waitThe mixture was left
3. stirringstirring overnight
4. customwas then quenched by the addition of 100 mL saturated aqueous NH4Cl solution
5. extractionThe mixture was extracted with 3×100 mL EtOAc
6. washThe combined organic layers were washed with water
7. dry with materialdried over MgSO4
8. customEvaporation of the volatiles at 80° C.

ORD record

ord-65248f9888e4463cace6a2677681e6e9

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598213B2