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

Participants

Reaction Conditions

Reaction Steps

(+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (185 mg, 0.47 mmol, prepared in example 17) and N-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide (168 mg, 0.56 mmol) were dissolved in 25 mL of n-propanol and 78 mg (0.56 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (5 mg) and the mixture refluxed at 90° C. for 4 hours. The reaction is worked up in a manner analogous to example 3. Purification by silica chromatography using a Chromatotron® was achieved eluting with 99:1 methylene chloride:methanol to afford 135 mg (66%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Provenance & Evidence