N-Methoxy-N-methylisonicotinamide → HCID 59354815, compound

Temperature

-78 °C

To a stirred solution of (1-ethynylcyclopentyloxy)trimethylsilane (2.0 g, 11.0 mmol) in dry THF (50 mL) was added n-BuLi (20.0 mL, 20.0 mmol, 1.6 M in hexane) drop wise at −78° C. under an inert atmosphere for a period of 10 min. After being stirred for 30 min at −78° C., a solution of compound N-methoxy-N-methylisonicotinamide (2.1 g, 13.2 mmol) in dry THF (10 mL) was added to the reaction mixture and stirring was continued for an additional 2 h at −78° C. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc (2×60 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography eluting with 5% EtOAc in Hexane to afford 1-(pyridin-4-yl)-3-(1-(trimethylsilyloxy)cyclopentyl) prop-2-yn-1-one (1.0 g, 32%) as an oil.

1. stirringstirring
2. waitwas continued for an additional 2 h at −78° C
3. customThe reaction mixture was quenched with a saturated NH4Cl solution
4. extractionextracted with EtOAc (2×60 mL)
5. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto obtain the crude product
10. customThe crude material was purified via silica gel column chromatography
11. washeluting with 5% EtOAc in Hexane

ORD record

ord-62d926cedd514905a30bbde7c1475290

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071595B2