1,4-Cyclohexadiene → HCID 67465629, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4 and benzyl-[3-chloro-4-(5-morpholin-4-yl-[1,6]naphthyridin-7-yl)-phenyl]-amine (164 mg, 0.32 mmol, 1 eq) in dry EtOH (3 mL) was added Pd(OH)2 (60 mg, 40% w/w) and 1,4-cyclohexanediene (600 μL, 6.30 mmol, 20 eq) under Ar(g). The mixture was heated at 80° C. overnight. Additional quantities of Pd(OH)2 (60 mg, 40% w/w) and 1,4-cyclohexanediene (400 μL, 4.10 mmol, 15 eq) were added, and the mixture was again heated at 80° C. overnight. Once cooled down, the reaction mixture was filtered through a short celite pad, eluted with MeOH (10 mL). The solvent was removed in vacuo and the residue was further purified by silica gel column chromatography, eluting with CH2Cl2/MeOH (1:0-49:1), to furnish the product, F, as a pale yellow solid (8.1 mg, 8%).

Provenance & Evidence