HCID 86690333, compound → HCID 86690332, compound

Participants

Reaction Steps

7-(7,7-Dibromo-6-oxo-2,3-di-p-tolyl-6,7-dihydro-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoic acid (mixture from step 1)(127 mg, 0.211 mmol) in dry THF (5 ml) under nitrogen was treated with 10% Pd(C) (22.48 mg, 0.021 mmol) and the mixture was stirred at RT under an atmosphere of hydrogen for 16 hours. The resulting mixture was filtered through Celite® and washed through with DCM. The filtrate was concentrated under reduced pressure and purification was carried out by chromatography on silica eluting with 0-100% EtOAc in iso-hexane. Further purification was carried out by dissolving the product in DCM (minimal) and loading onto a 20 cm×20 cm preparative TLC plate. The plate was run using a solvent system of 75% EtOAc in iso-hexane (300 ml) and the appropriate strip of Si was scrapped off the plate. The silica was suspended in 10% MeOH/DCM and sonicated. The suspension was filtered, rinsing the solid with 10% MeOH/DCM. The filtrate was concentrated under reduced pressure to afford the title compound;

Provenance & Evidence