Potassium Carbonate → HCID 178502289, compound

Participants

Reaction Conditions

Reaction Steps

Methyl (S)-1-((S)-8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamate (100 mg, 0.197 mmol), bis(pinacolato)diboron (51 mg, 0.2 mmol), potassium acetate (58 mg, 0.591 mmol), and Pd(dppf)Cl2 (15 mg, 0.02 mmol) were all weighed out in a glass pressure vessel and anhydrous 1,4-Dioxane (1 mL) was added. The mixture was bubbled with nitrogen gas for about 5 min. The vessel was then capped and sealed and heated in an oil bath at 95° C. overnight with continuous stirring. The reaction vessel was cooled down to room temperature and (S)-tert-butyl 2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (83 mg, 0.29 mmol), 2M K2CO3 (296 uL), and Pd(PPh3)4 (23 mg, 0.02 mmol) were all added along with 1 mL of DMSO or 1,4-dioxane and the mixture was bubbled with nitrogen gas for 5 minutes. The vessel, again, was capped, sealed and placed in an oil bath at 100° C. for 4 hours.

Provenance & Evidence