Ethyl Acetate → 7-(2-Fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

Temperature

-60 °C

7-(2-Fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one (0.5 g, 1.27 mmol) in DCM (10 mL) was added to silver tetrafluoroborate (0.74 g, 3.81 mmol) in DCM (10 mL) previously degassed with nitrogen at −60° C. and the resulting mixture was stirred at −60° C. for 30 minutes. This was followed by the addition of iodine monochloride (1.3 mL, 1.399 mmol) and continued stirring for a further 30 minutes at −60° C. to −50° C. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was diluted with DCM, quenched with sodium thiosulphate solution, filtered through celite and the filtrate was extracted with DCM. The organic layer was washed with NH3 solution, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 0.45 g of the product (80% yield).

1. custompreviously degassed with nitrogen at −60° C.
2. stirringcontinued stirring for a further 30 minutes at −60° C. to −50° C
3. customquenched with sodium thiosulphate solution
4. filtrationfiltered through celite
5. extractionthe filtrate was extracted with DCM
6. washThe organic layer was washed with NH3 solution, brine solution
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

ORD record

ord-174855e6bb934dc49d06592e2602c351

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466289B2