Sodium Carbonate → N-(5-(2-fluorobenzyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluorobenzyl bromide (33 μL, 0.27 mmol), N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (100 mg, 0.27 mmol), trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) (11 mg, 0.014 mmol), and sodium carbonate (145 mg, 1.37 mmol) in degassed tetrahydrofuran (1.33 mL) and water (0.66 mL) was stirred at 80° C. for 16 h. The reaction was then diluted with 6 mL of DCM and 2 mL of water and the mixture was filtered over a phase separator. The organic phase was evaporated to dryness in vacuo to afford a brown oil in. Purification by silica flash column chromatography (EtOAc/heptane: from 0% to 60% of EtOAc) afforded the title compound as an oil (63.1 mg, 66%). MS (ESI): m/z [M−H]− 346.0

Provenance & Evidence