Dimethylformamide → HCID 58349833, compound

To a solution of N,N-dimethylformamide (717 mg) in dichloromethane (20 mL) was added oxalyl chloride (1.13 g) under ice-cooling under an argon atmosphere, and the mixture was stirred for 10 min. To the obtained suspension was added a solution of 2-fluoro-3-{3-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrol-2-yl}pyridine (1.50 g) in dichloromethane (5 mL) and the mixture was stirred under refluxing conditions for 10 hr. The reaction mixture was cooled under ice-cooling, 1 mol/L aqueous sodium hydroxide solution (30 mL) was added and the mixture was stirred for 15 min. The solvent was evaporated to a half volume under reduced pressure and the residue was partitioned by adding ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual solid was washed with diisopropyl ether (30 mL) and filtered by suction to give the title compound as a colorless solid (yield 726 mg, 78%).

1. temperaturecooling under an argon atmosphere
2. stirringthe mixture was stirred under refluxing conditions for 10 hr
3. temperatureThe reaction mixture was cooled under ice-
4. temperaturecooling
5. stirringthe mixture was stirred for 15 min
6. customThe solvent was evaporated to a half volume under reduced pressure
7. customthe residue was partitioned
8. additionby adding ethyl acetate
9. extractionThe separated aqueous layer was extracted again with ethyl acetate
10. washCombined organic layers were washed with saturated brine
11. dry with materialdried over anhydrous sodium sulfate
12. concentrationconcentrated under reduced pressure
13. washThe residual solid was washed with diisopropyl ether (30 mL)
14. filtrationfiltered by suction

ORD record

ord-a99dc2ebbeeb43ac83d2c35f3e2e17d3

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969387B2