Phthalimide → HCID 11609941, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-imidazo[4,5-b]pyridin-1-yl-4-methyl-pent-2-enoic acid methyl ester (1 eq) was added palladium, 10 wt. % on activated carbon, (10%) and left stirring under an atmospheric pressure of hydrogen for 2 days. After the catalyst was filtered off, the mixture was concentrated and dissolved in ethanol. To this solution was added sodium borohydride (4 eq) at room temperature. The reaction mixture was heated in a 50° C. oil bath for 60 minutes and then quenched by addition of H2O. Once the solvent was removed in vacuto, a solution of the residue in dichloromethane was washed with NaCl (sat.), dried over sodium sulfate, filtered, and concentrated. To a solution of the residue in THF was added dropwise diethyl azodicarboxylate (1 eq), triphenyl phosphine (1 eq), and phtalimide (1 eq). The yellow solution was stired at room temperature overnight and the solution was concentrated. The crude solid was treated with 3 N HCl and ethyl acetate. Once the aqueous layer was seperated, it was added to ethyl acetate and treated with sodium bicarbonate under vigorous stirring to obtain an approximate basic pH 7. The organic phase was seperated and washed with NaCl (sat.), dried over sodium sulfate, filtered, and concentrated to give 2-(4-imidazol[4,5-b]pyridin-1-yl-4-methyl-pentyl)-isoindole-1,3-dione (40%). MH+(349)

Provenance & Evidence