Sodium Carbonate → (S)-methyl 3-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To (S)-N-(5-(chloromethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.160 mmol, 46 mg) in THF (1 mL) was added methyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(trifluoromethyl)benzoate (0.160 mmol, 50.5 mg), Bromo(N-succinimidyl)bis-(triphenylphosphine)palladium(II) (7.99 μmol, 6.46 mg) and sodium carbonate (1.000 mmol, 0.5 mL). The reaction was heated to 100° C. for 10 minutes by microwave irradiation before diluting with DCM and filtering through a hydrophobic frit. The solvent was removed in vacuo before redissolving in MeCN (500 μL) and purifying by reverse phase preparative chromatography to give (S)-methyl 3-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate (23.2 mg, 31.9%). MS (ESI): m/z [M+H]+ 456.0

Provenance & Evidence