1-Bromo-4-chlorobutane → HCID 18995649, compound

Participants

Reaction Steps

A solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 3.43 mmole, Example 1 Part E) in tetrahydrofuran (30 mL) was cooled to -78° C. Butyllithium (1.4 mL of 2.5M in hexanes, 3.5 mmole) was added dropwise followed by the addition of 1-bromo-4-chlorobutane (4 mL, 34 mmole). The reaction mixture was allowed to warm to ambient temperature then it was quenched with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel eluting with 10% ethyl acetate in hexanes v/v) to provide 1.5 g of N,N-bis(phenylmethyl)-2-(5-chloropentyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Provenance & Evidence