Phosphorus oxychloride → HCID 86669012, compound

A stirred solution of 2-(2,6-dichlorophenyl)-7-fluorothiazolo[5,4-c]pyridine 5-oxide (0.095 g, 0.30 mmol) in phosphoryl chloride (3 mL) was heated under reflux for 0.5 hour and then at 110° C. for 15 minutes. The reaction was repeated on a larger scale by reacting 2-(2,6-dichlorophenyl)-7-fluorothiazolo[5,4-c]pyridine 5-oxide (6.4 g, 17.0 mmol) with phosphoryl chloride (100 mL) and by heating the mixture under reflux for 30 minutes. After cooling to room temperature, the mixture was left standing at room temperature for 18 hours and then heated at reflux temperature for 15 minutes. The two crude reaction mixtures were combined and the volatiles were removed under reduced pressure. The crude residue was dissolved in EtOAc (200 mL) and washed with a saturated solution of potassium carbonate, followed by water, then dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-20% EtOAc in pentane to afford the title compound as a white solid (3.42 g, 49% yield). 1H NMR (400 MHz, CDCl3): δ 8.39 (d, J=1.9 Hz, 1H), 7.53-7.41 (m, 3H).

1. temperatureunder reflux for 0.5 hour
2. temperatureby heating the mixture
3. temperatureunder reflux for 30 minutes
4. waitthe mixture was left
5. waitstanding at room temperature for 18 hours
6. temperatureheated
7. temperatureat reflux temperature for 15 minutes
8. customThe two crude reaction mixtures
9. customthe volatiles were removed under reduced pressure
10. dissolutionThe crude residue was dissolved in EtOAc (200 mL)
11. washwashed with a saturated solution of potassium carbonate
12. dry with materialdried (Na2SO4)
13. concentrationconcentrated under reduced pressure
14. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-20% EtOAc in pentane

ORD record

ord-83607517f5a74e7e822a3354bc344a00

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697708B2