Pyridine → 2-Methylimidazo[1,2-a]pyridine-3-carbonitrile

To a mixture of 2-methylimidazo[1,2-a]pyridine-3-carboxamide (3.50 g, 20 mmol) produced in the above, pyridine (4.85 mL, 60 mmol) and tetrahydrofuran (50 mL) was added dropwise a solution of trifluoroacetic anhydride (4.24 mL, 30 mmol) in tetrahydrofuran (10 mL) under ice-cooling. The mixture was stirred at room temperature for 1 hr, saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with ethyl acetate/diisopropyl ether to give the title compound (2.5 g, 80%) as a pale-brown solid.

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe collected organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationthe insoluble material was filtered off
6. concentrationThe filtrate was concentrated under reduced pressure
7. washthe obtained residue was washed with ethyl acetate/diisopropyl ether

ORD record

ord-ec246c45e1a94ff3a9afac20584c52a6

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090601B2