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

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Reaction Conditions

Reaction Steps

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).

Provenance & Evidence