Dimethylformamide → Imidazo[1,5-a]pyridine-3-carboxaldehyde

Temperature

-40 °C

To imidazo[1,5-a]pyridine (2.337 g, 19.78 mmol) in tetrahydrofuran (40 mL) was added n-butyl lithium (2.5 M in hexane, 15.76 mL, 39.4 mmol) at −40° C. The mixture was stirred at −40° C. for 3.5 hours, followed by the addition of dimethylformamide (3.1 mL, 40 mmol). The reaction mixture was stirred at 25° C. overnight and quenched with water. The mixture was then partitioned between dichloromethane (80 mL) and water (15 mL). The organic phase layer was dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by chromatography eluting with 0-50% ethyl acetate/dichloromethane to give the title compound (1.78 g, 62% yield).

1. stirringThe reaction mixture was stirred at 25° C. overnight
2. customquenched with water
3. customThe mixture was then partitioned between dichloromethane (80 mL) and water (15 mL)
4. dry with materialThe organic phase layer was dried with anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude material was purified by chromatography
8. washeluting with 0-50% ethyl acetate/dichloromethane

ORD record

ord-9b23448507d544da95ee28241ed8cf2d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834043B2