Dimethylformamide → HCID 86051826, compound

Participants

Reaction Steps

A solution of n-butyllithium in hexanes (2.5 M, 45.5 mL, 1.15 equivalents) was added dropwise to a stirred, −78° C. solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (prepared as described in Example 32 of U.S. Pat. No. 4,689,338, 25.64 g) in tetrahydrofuran (450 mL). The solution was stirred for 10 minutes, then DMF (20.1 mL, 2.3 equivalents) was added. The reaction mixture was allowed to warm to room temperature over 1 hour. The volatiles were removed under reduced pressure and the residue was portioned between ethyl acetate (400 mL) and brine (400 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a brown solid that was purified by flash chromatography (silica gel, gradient elution with 0.5-1% methanol in dichloromethane) to provide 10.5 g of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde.

Provenance & Evidence