Sodium Carbonate → HCID 58382356, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g, 0.056 mmol, Preparation #MM.1) and PdCl2(dppf)•DCM adduct (0.0046 g, 0.0056 mmol) in THF (1 mL) was added a solution of phenylboronic acid (0.12 g, 0.098 mmol) and Na2CO3 (0.009 g, 0.084 mmol) in water (0.25 mL). The reaction mixture was heated to about 60° C. After about 6 h, the reaction mixture was cooled to ambient temperature and was diluted with EtOAc (5 mL) and brine (5 mL). The organic layer was separated and concd in vacuo. The residue was dissolved in 1,4-dioxane (5 mL) and NaOH (2 N aqueous, 1 mL) was added. The reaction mixture was heated to about 65° C. After about 15 h, the reaction mixture was cooled to ambient temperature and HCl (1 N aqueous, 3 mL) and EtOAc (5 mL) were added. The organic layer was separated, concd in vacuo, and the residue was purified by chromatography on silica gel (12 g) eluting with 20-80% EtOAc in DCM to provide 1-cyclohexyl-3-phenyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.005 g, 28%) as a solid: LC/MS (Table 1, Method a) Rt=2.75 min; MS m/z: 317 (M+H)+.

Provenance & Evidence