Sodium Carbonate → HCID 67414081, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (25)-tert-butyl 2-(4-(trifluoromethylsulfonyloxy)cyclohex-3-enyl carbamoyl)pyrrolidine-1-carboxylate (2) (1.65 g, 3.73 mmol) and (5)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (3) (1.95 g, 4.44 mmol) in THF (19 mL), Pd(PPh3)2Cl2 (130 mg, 0.185 mmol) and aqueous Na2CO3 (2M, 7.5 mL, 15 mmol) were added under N2 protection at rt. The reaction mixture was heated at 80° C. overnight, and cooled to rt. The mixture was then filtered through a CELITE™ pad and washed with ethyl acetate. The combined organic phases were concentrated to provide the crude product, which was purified by silica gel column chromatography (n-hexane/ethyl acetate, 1:2) to afford (2S)-tert-butyl 2-(4-(4-(2-((5)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)cyclohex-3-enylcarbamoyl)pyrrolidine-1-carboxylate (4) (2.1 g, 93% yield).

Provenance & Evidence