Dichloromethane → 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) and PdCl2(dppf).DCM (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 mixture was heated to about 60° C. After about 6 h, the mixture was cooled to rt and was diluted with EtOAc (5 mL) and brine (5 mL). The organic layer was separated and concentrated in vacuo. The residue was dissolved in 1,4-dioxane (5 mL) and aqueous NaOH (2 N, 1 mL) was added. The mixture was heated to about 65° C. After about 15 h, the mixture was cooled to rt and aqueous HCl (1 N, 3 mL) and EtOAc (5 mL) were added. The organic layer was separated, concentrated in vacuo, and the residue was purified by chromatography on silica gel (12 g) eluting with 20 to 80% EtOAc in DCM to provide 1-cyclohexyl-3-phenyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.005 g, 28%): LC/MS (Table 2, Method a) Rf=2.75 min; MS m/z: 317 (M+H)+. Syk IC50=C.

Provenance & Evidence