Acetic Acid → HCID 58382495, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (0.29 mL, 2.0 mmol) in THF (5 mL) was cooled to about −70° C. then treated with n-BuLi (1.6 M in hexanes, 1.1 mL, 1.8 mmol) keeping the internal temperature of the reaction at about −60 to −70° C. After about 15 min the mixture was warmed to about 20° C. The mixture was added slowly to the 1-methyl-6-tosyl-1,2,3,6-tetrahydrodipyrrolo[2,3-b:2′,3′-d]pyridine (0.300 g, 0.916 mmol) in THF (5.0 mL) at about −60° C. to −70° C. The mixture was stirred at about −70° C. for about 1 h then iodine (0.27 g, 1.1 mmol) in THF (2 mL) was added keeping the temperature of the mixture at about −65 to −70° C. The mixture was stirred for about 1 h at about −70° C. then AcOH (0.16 mL, 2.8 mmol) and about 1 mL saturated aqueous NH4Cl were added. The mixture was warmed to rt then diluted with water (10 mL), saturated aqueous NaHCO3 (5 mL) and DCM (50 mL). The layers were separated then the aqueous layer was extracted with DCM (15 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was triturated in EtOAc (8 mL) then filtered and washed with EtOAc (2 mL) to give the title compound (0.24 g, 58%): LC/MS (Table 2, Method a) Rt=2.52 min; MS m/z 454 (M+H)+.

Provenance & Evidence