2-(Bromomethyl)-5-(trifluoromethyl)furan → N-[(2s)-5-{[5-(Trifluoromethyl)furan-2-Yl]methyl}-2,3-Dihydro-1h-Inden-2-Yl]propane-2-Sulfonamide

Participants

Reaction Conditions

Reaction Steps

2-(bromomethyl)-5-(trifluoromethyl)furan (0.123 mmol, 28.2 mg), (S)—N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.123 mmol, 45 mg) and Bromo(N-succinimidyl)bis-(triphenylphosphine)palladium(II) (6.16 μmol, 4.98 mg) were suspended in THF (1 mL) and 2M NaCO3 (0.5 mL) added. The mixture was heated to 100° C. for 10 min. After this time the reaction mixture was irradiated for a further 20 min at 100° C. before standing overnight. The mixture was concentrated to remove THF before partitioning between DCM/H2O. The organic layer was collected and dried using a hydrophobic filter tube. Concentration and purification on basic HPLC gave the title compound (7.5 mg, 0.019 mmol, 15.7%). MS (ESI): m/z [M−H]− 386.3.

Provenance & Evidence