Potassium Hydroxide → HCID 57831039, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.067 g, 0.16 mmol), 0.4 mL dioxane, 0.4 mL water, Pd2(dba)3 (0.009 g, 0.01 mmol), 2-di-t-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (0.008 g, 0.02 mmol), and freshly ground KOH (0.038 g, 0.67 mmol) in a sealed tube under N2 was stirred at 100° C. for 15 h. The resulting orange-black mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water, with a few drops of ethanol added to reduce emulsions. The aqueous layer was extracted with 5 mL of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated to an orange oil. Silica gel chromatography (20→40% EtOAc/hexanes) afforded 0.029 g (51%) of 7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-1,5-dihydro-pyrrolo[2,3-b]pyrazin-2-one as a pale yellow solid.

Provenance & Evidence