Sodium Hydroxide → HCID 68656890, compound

Participants

Reaction Steps

A solution of methyl 5-[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]pyridine-2-carboxylate (132 mg, 0.327 mmol) in THF (3 ml) was cooled to −78° C., followed by the dropwise addition of lithium aluminum hydride (0.360 ml, 1M THF solution, 0.360 mmol). After 1 hour, the mixture was treated with water (15 uL), 2N aqueous sodium hydroxide (15 uL) and water (45 uL). The mixture was warmed to room temperature, diluted with diethyl ether and treated with magnesium sulfate. After stirring for 30 minutes, the mixture was filtered through celite and concentrated in vacuo. The residue was purified via silica gel chromatography (methanol/dichloromethane gradient), providing the titled compound: LRMS m/z (M+H) 375.0 and 377.0 found, 375.1 and 377.1 required.

Provenance & Evidence