Methyl iodide → HCID 86691842, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask, {3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl}acetonitrile (14-48) (45 mg, 0.14 mmol) was added and dissolved in THF (1.3 ml) under nitrogen and cooled to −78° C. 1 M Sodium bis(hexamethylsilyl)amide (0.18 ml, 0.18 mmol) was added slowly to the cooled solution, followed by Methyl iodide (25 mg, 0.18 mmol). The cooled solution was stirred for 30 minutes, allowed to warm to room temperature and stirred for 10 minutes. The reaction was diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 2-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl}propanenitrile (33-1), HRMS (M+H)+: observed=349.2032, calculated=349.2023 and 2-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl}-2-methylpropanenitrile (33-2); HRMS (M+H)+: observed=363.2186, calculated=363.2179.

Provenance & Evidence