Triethylamine → HCID 67422163, compound

Participants

Reaction Steps

To a 0° C. solution of [1-(2-nitro-benzenesulfonyl)-azetidin-3-yl]-methanol (165 mg, 0.606 mmol) in EtOAc (15 mL) was added Et3N (0.101 mL, 0.727 mmol) then mesyl chloride (0.052 mL, 0.666 mmol). The reaction mixture was stirred for 1 hour at room temperature. The precipitate was filtered through a plug of Celite and was washed with EtOAc. The filtrate was concentrated and the crude mesylate was dissolved in DMF (5 mL). To this solution was added DIPEA (0.211 mL, 1.20 mmol) and 3,3′-dimethyl-1′,2′,3′4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (162 mg, 0.606 mmol) and the mixture was heated at 80° C. for 17 hour Saturated NaHCO3 (15 mL) was added and the mixture was extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by radial chromatography on silica gel (Et2O saturated with NH4OH) to give 3,3′-dimethyl-1′-[1-(2-nitro-benzenesulfonyl)-azetidin-3-ylmethyl]-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (168 mg, 53%).

Provenance & Evidence