Dimethylformamide → HCID 57636804, compound

Temperature

60 °C

Sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.7 mmol) was mixed with 3-5 ml of dry dimethylformamide and 3-fluorophenol (0.244 ml, 2.7 mmol) was added to the stirred suspension. When the gas evolution was ceased the reaction mixture was heated at stirring at 60° C. and 5-bromo-2-nitropyridine (0.5 g, 2.5 mmol) was added to the reaction mixture in one portion. The reaction-mixture was stirred at 60° C. for about 12 hours. The reaction mixture was then mixed with 50 ml of water and extracted into methylene chloride (3×20 ml). Organic extract was washed with water and brine, dried over magnesium sulfate and concentrated by rotary evaporation. The resulting mixture was purified by column chromatography on silica (30 g, EtOAc/hexane 1:3) to give 190 mg (33% yield) of desired product.

1. additionwas added to the stirred suspension
2. temperaturewas heated
3. stirringThe reaction-mixture was stirred at 60° C. for about 12 hours
4. extractionextracted into methylene chloride (3×20 ml)
5. extractionOrganic extract
6. washwas washed with water and brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated by rotary evaporation
9. customThe resulting mixture was purified by column chromatography on silica (30 g, EtOAc/hexane 1:3)

ORD record

ord-369e19b26d244264bd6f4b555bd8b749

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517992B2