1,1'-Carbonyldiimidazole → 3-[4-(1-(isopropylsulfonylaminocarbonyl)-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dipropylphenyl-methyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A 15 mL capacity high pressure vessel equipped with a magnetic stir bar was charged with a solution of 0.230 g (0.42 mmol) of the product of Example 13 in 4.0 mL of anhydrous THF and 0.172 g (1.06 mmol) of 1,1'-carbonyldiimidazole was added. The vessel was sealed and the contents were stirred and heated at 80° C. for 4 hours. The reaction was then cooled to room temperature, opened and a solution of 0.130 g (1.06 mmol) of isopropylsulfonamide and 158 μL (1.06 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 4 mL THF was added. The reaction vessel was resealed and then stirred and heated at 80° C. overnight. The reaction vessel was then cooled, opened and the contents were partitioned between water and EtOAc. The organic layer was separated washed with 10% aqueous NaHSO4, brine, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted first with 250 mL of CHCl3 /MeOH/NH4OH (95:5:0.5), next with 200 mL of CHCl3 /MeOH/NH4OH (92:8:0.5), and finally with 200 mL of CHCl3 /MeOH/NH4OH (90:10:0.5). Evaporation of the purified fractions and drying in vacuo afforded 0.074 g (27%) of the title compound.

Provenance & Evidence