Pyridine → 4-fluoro-N-[3-(methylsulfanyl)phenyl]-2-nitrobenzenesulfonamide

Temperature

0 °C

A solution of 3-(methylsulfanyl)aniline (658 mg, 4.73 mmol) and pyridine (995 uL, 18.9 mmol) was cooled to 0° C. under N2 before the dropwise addition of bis(trimethylsilyl)trifluorocetamide (1.76 mL, 9.45 mmol) over 5 min. After stirring for 5 min at 0° C., a solution of 4-fluoro-2-nitrobenzenesulfonyl chloride (1.19 g, 4.97 mmol) in 1,4-dioxane (7 mL) was added dropwise over 15 min. The mixture was stirred at rt for 1 h, then at 100° C. for 30 min. After cooling to rt, the mixture was concentrated in vacuo and partitioned between DCM and 1M aqueous HCl (25 mL each). The phases were separated and the aqueous layer extracted with DCM (2×25 mL). The combined organic layers were concentrated in vacuo and purified by gradient flash chromatography, eluting with 5-50% EtOAc in heptane to yield the title compound (865 mg, 2.53 mmol).

1. stirringThe mixture was stirred at rt for 1 h
2. waitat 100° C. for 30 min
3. temperatureAfter cooling to rt
4. concentrationthe mixture was concentrated in vacuo
5. custompartitioned between DCM and 1M aqueous HCl (25 mL each)
6. customThe phases were separated
7. extractionthe aqueous layer extracted with DCM (2×25 mL)
8. concentrationThe combined organic layers were concentrated in vacuo
9. custompurified by gradient flash chromatography
10. washeluting with 5-50% EtOAc in heptane

ORD record

ord-b474e711e6b8450c99ae308833b39f53

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249160B2