Ammonia → HCID 178437490, compound

2-Ethyl-3H-imidazo[4,5-b]pyridine (U.S. Pat. No. 5,332,744; 4.00 g, 27.2 mmol) was dissolved in chloroform (45 mL), and the solution was added with m-chloroperbenzoic acid (5.18 g, 29.9 mmol) followed by stirring at room temperature for 5 hr. The reaction mixture was concentrated, added with ethyl acetate and water, and partitioned between ethyl acetate and water. The aqueous layer was concentrated and the residue was dissolved in chloroform (8 mL). Phosphorus oxychloride (24 mL, 257 mmol) was added thereto and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured onto ice, neutralized with aqueous ammonia, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate (30 mL) was added to the residue and the precipitated solid was collected by filtration to give the title compound (3.32 g, 67%).

1. concentrationThe reaction mixture was concentrated
2. additionadded with ethyl acetate and water
3. custompartitioned between ethyl acetate and water
4. concentrationThe aqueous layer was concentrated
5. dissolutionthe residue was dissolved in chloroform (8 mL)
6. stirringthe mixture was stirred at room temperature for 2 hr
7. additionThe reaction mixture was poured onto ice
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with brine
10. dry with materialdried over anhydrous magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. additionEthyl acetate (30 mL) was added to the residue
13. filtrationthe precipitated solid was collected by filtration

ORD record

ord-95e4a7a194654af487e00c0fb4eb42f1

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242151B2