Sodium Hydroxide → 2,3-Dimethyl-8-(2,6-diethylbenzylamino)-imidazo[1,2-a]pyridine

8-amino-2,3-dimethyl-imidazo[1,2-a]pyridine (0.33 g, 2.0 mmol) and 2,6-diethylbenzaldehyde (0.36 g, 2.2 mmol) were dissolved in methanol (7 ml). ZnCl2 (0.30 g, 2.2 mmol) and subsequently NaBH3CN (0.14 g, 2.2 mmol) in small portions were added and the mixture was refluxed under argon for 3 hours, cooled and then poured over an aqueous 1M NaOH solution (10 ml). The resultant yellow suspension was extracted with DCM (3×25 ml) and the combined organic solutions were washed with brine, dried over Na2SO4 and then removed. The oily residue (0.4 g) was purified by flash chromatography (DCM-EtOAc 0%-20% EtOAc) to give 0.34 g. Treatment of this oily product with hexane (2 ml) afforded 0.14 g (23%) as off-white crystals.

1. temperaturethe mixture was refluxed under argon for 3 hours
2. temperaturecooled
3. extractionThe resultant yellow suspension was extracted with DCM (3×25 ml)
4. washthe combined organic solutions were washed with brine
5. dry with materialdried over Na2SO4
6. customremoved
7. customThe oily residue (0.4 g) was purified by flash chromatography (DCM-EtOAc 0%-20% EtOAc)
8. customto give 0.34 g

ORD record

ord-754303612eb64590bcff75744c3659ab

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265415B1