Morpholine → HCID 67382101, compound

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (1.0 g), (+)-2,2′-bis(diphenylphosphino)-1,1′binaphthyl (BINAP, 0.089 g), tris(dibenzylideneacetone)dipalladium(0) (0.074 g), sodium tert-butoxide (0.320 g,), morpholine (0.230 mL,) and toluene (4.8 mL) were added to a scintillation vial. The vial was sequentially flushed with nitrogen, sealed with a Teflon-lined cap, placed in an oil bath, and heated at 80° C. for 16 hours. The reaction mixture was cooled to ambient temperature and then transferred to a round bottom flask. The volatiles were removed under reduced pressure and the residue was purified by column chromatography on a Biotage Horizon™ High Performance Flash Chromatography instrument using a silica gel cartridge. The purification was carried out eluting with chloroform:CMA in a gradient from 98:2 to 75:25. 2-Ethoxymethyl-1-(3-isopropoxypropyl)-7-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline was isolated as a red-orange oil (1.32 g).

Provenance & Evidence