8-Hydroxyquinoline → HCID 67386074, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL flask was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide (100 mg, 0.17 mmol, copper(I) iodide (1.7 mg, 0.009 mmol), 8-hydroxyquinoline (2.5 mg, 0.017 mmol) and potassium phosphate tribasic (74 mg, 0.34 mmol) under argon atmosphere. Cyclohexanol (1.82 mL, 17.3 mmol) was added and the reaction mixture was heated at 120° C. for 24 h. The reaction mixture was allowed to reach room temperature and then diluted with EtOAc (10 mL). The slurry was filtered over a celite pad and the filtrate was evaporated under vacuum. The crude residue was purified by preparative TLC (SiO2, Hex:EtOAc, 1:1×2) to give 52 mg (50%) of 2-cyclohexyloxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide. (M+Na)+=619.

Provenance & Evidence