Boron trifluoride etherate → N-[1-(6-Bromo-pyridin-2-yl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide

To a solution of N-[1-(6-bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethyl]-2-chloro-acetamide (9.0 g, 21.861 mmol) in ethanethiol (30 ml) and BF3.Et2O (9.3 g, 141.93 mmol) was added at 0° C. and stirred for 10 min. Stirring was continued for 3 h at rt. Reaction mixture was quenched with saturated NaHCO3 solution and the product formed was extracted with ethyl acetate. Organic layer was separated and washed with brine solution, followed by drying over anhydrous Na2SO4. Organic layer was concentrated under reduced pressure and purified by column chromatography using 2% methanol in chloroform to obtain title compound as a brown liquid. Yield=5.5 g (77%). TLC (10% methanol in chloroform) Rf=0.51; LCMS: RtH8=0.916, [M+1]=322.9 and 324.8; HPLC RtH9=5.931 min (89%); 1H NMR (400 MHz, CDCl3): δ 8.27 (s, 1H), 7.56 (t, 1H), 7.42-7.39 (m, 2H), 4.38 (s, 2H), 4.09-4.07 (m, 4H), 3.95 (d, 2H).

1. stirringStirring
2. waitwas continued for 3 h at rt
3. customReaction mixture
4. customwas quenched with saturated NaHCO3 solution
5. customthe product formed
6. extractionwas extracted with ethyl acetate
7. customOrganic layer was separated
8. washwashed with brine solution
9. dry with materialby drying over anhydrous Na2SO4
10. concentrationOrganic layer was concentrated under reduced pressure
11. custompurified by column chromatography

ORD record

ord-3005d89d72e94b4090b685e9090052da

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865712B2