Ethanethiol → S-ethyl 2-bromopyridine-4-carbothioate

Triethylamine (3.0 g, 29.7 mmol) was added to a suspension of 2-bromo-isonicotinic acid (5.0 g, 24.8 mmol) in anhydrous dichloromethane (50 mL). The mixture was stirred at room temperature for 10 minutes, cooled to 0° C. and isobutyl chloroformate (3.6 g, 26.0 mmol) was added dropwise. The reaction mixture was then stirred at 0° C. for 30 minutes, ethanethiol (1.6 g, 25.99 mmol) was then added dropwise and the stirring was continued for an additional 2 h at 0° C. The reaction mixture was diluted with dichloromethane (100 mL) and water (100 mL). The organic layer was separated, washed with water, dried over is sodium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography using 15% ethyl acetate in hexane to afford the title compound (5.0 g, 80%).

1. temperaturecooled to 0° C.
2. stirringThe reaction mixture was then stirred at 0° C. for 30 minutes
3. waitthe stirring was continued for an additional 2 h at 0° C
4. customThe organic layer was separated
5. washwashed with water
6. customdried
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash column chromatography

ORD record

ord-e932dd09e7a54dc4bbbf7286afd00ebb

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030500B2