proline dl-form → HCID 59540709, compound

Participants

Reaction Conditions

Reaction Steps

DMSO (1.5 mL) was added to a mixture of copper iodide (10.6 mg; 0.056 mmol), d,l-proline (12.8 mg; 0.11 mmol), potassium carbonate (113 mg; 0.81 mmol), and 1-[2-(3-Iodo-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (150 mg; 0.37 mmol). Isopropyl amine (0.315 mL; 0.219 g, 3.7 mmol) was added and the resulting mixture was stirred at 110° C. (oil bath) for 24 hrs. The reaction mixture was quenched with water and extracted 3 times with EtOAc. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated to give a yellow oil. Preparative HPLC afforded 6.1 mg (5% yield) of 1-[2-(3-Isopropylamino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid

Provenance & Evidence