Potassium Carbonate → HCID 68668231, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step 1, ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-ene-1-carboxylate (6.65 g, 22.0 mmol) in dioxane (125 mL) was added potassium carbonate (4.56 g, 33.0 mmol), PPh3 (0.346 g, 1.32 mmol), bis(pinacolato)diboron (6.15 g, 24.20 mmol), and PdCl2(PPh3)2 (0.463 g, 0.66 mmol). The mixture was then heated to 80° C. overnight. This solution was then cooled to r.t. and added to a mixture of 1-bromo-4-iodo-2-methoxybenzene (6.86 g, 21.92 mmol), PdCl2(dppf) (0.481 g, 0.657 mmol), potassium carbonate (9.09 g, 65.7 mmol). This mixture was then heated to 80° C. overnight. The mixture was then cooled to r.t., diluted with EtOAc (300 mL) and washed with brine and aqueous KHSO4. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo. The crude material was then purified on silica (100% DCM) to give impure product which was repurified on silica (gradient elution, 5-20% EtOAc/hexanes) to give the title compound.

Provenance & Evidence