Diisobutylaluminum hydride → Imidazo(1,2-a)pyridine-8-carbaldehyde

Temperature

-78 °C

To a solution of methyl imidazo[1,2-a]pyridine-8-carboxylate (1.76 g, 10 mmol) in toluene was added DIBAL (1M/THF, 20 ml) at −78° C. dropwise. The mixture was stirred at −78° C. for 1 h, quenched with MeOH (2 mL) and saturated NH4Cl solution (50 mL) and warmed up to rt. The mixture was continued to stir at rt for 1 h and diluted with DCM (60 mL). The aqueous layer was extracted with DCM (60 mL) twice. The combined organic layer was dried over MgSO4 and concentrate. The residue was purified on silica gel with 10% MeOH/DCM to give imidazo[1,2-a]pyridine-8-carbaldehyde (0.8 g, 55%). LRMS (M+H+) m/z 147.1.

1. customquenched with MeOH (2 mL) and saturated NH4Cl solution (50 mL)
2. temperaturewarmed up to rt
3. stirringto stir at rt for 1 h
4. additiondiluted with DCM (60 mL)
5. extractionThe aqueous layer was extracted with DCM (60 mL) twice
6. dry with materialThe combined organic layer was dried over MgSO4
7. concentrationconcentrate
8. customThe residue was purified on silica gel with 10% MeOH/DCM

ORD record

ord-2ff1c0bc860e4ec4a5be7b647d33d8f7

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018210B2