Potassium Carbonate → (+,-) Trans Propane-2-sulfonic acid [2-(3'-methanesulfonylamino-biphenyl-4-yl)-cyclopentyl]-amide

Participants

Reaction Conditions

Reaction Steps

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (235 mg, 0.60 mmol, prepared in example 2) and N-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide (213 mg, 0.72 mmol) were dissolved in 25 mL of n-propanol and 25 mg (0.18 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (7 mg) and the mixture refluxed at 90° C. for 4 hours. The reaction is worked up as in preparation 6. Purification by silica chromatography using a Chromatotron® was achieved eluting with 90:10 methylene chloride:ethyl acetate to afford 225 mg (86%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Provenance & Evidence