Diisobutylaluminumhydride → HCID 89690255, compound

To a stirred solution of ethyl 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carboxylate (1.0 g) in DCM (20 ml) was added a solution of diisobutylaluminum hydride (1.0 M toluene solution, 3.7 ml) at −78° C. The resultant mixture was stirred at the same temperature for 2 h. The reaction mixture was then quenched with a mixture of MeOH (2 ml) and water (2 ml) at −78° C. This reaction mixture was then acidified with a few drops of 5 M HCl, and washed with saturated NaHCO3 solution (20 ml). The mixture was extracted with EtOAc (3×150 ml), and the extract was washed with brine (100 ml), dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (600 mg) as an off-white solid.

1. customThe reaction mixture was then quenched with a mixture of MeOH (2 ml) and water (2 ml) at −78° C
2. washwashed with saturated NaHCO3 solution (20 ml)
3. extractionThe mixture was extracted with EtOAc (3×150 ml)
4. washthe extract was washed with brine (100 ml)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by silica gel column chromatography (MeOH/DCM)

ORD record

ord-9fc31f64075049209e069927b4aad079

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2