1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

Participants

Reaction Steps

At 0° C. and under protective atmosphere, a solution of 2-propanesulfonyl chloride (11.87 mL, 121 mmol) in DCM (121 mL) was added gradually to a solution of 5-bromo-2,3-dihydro-1H-inden-1-amine (12.8 g, 60.4 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.83 mL, 32.1 mmol) in dichloromethane (300 mL). The reaction was stirred at rt overnight. The reaction mixture was washed with 1N KHSO4 (1×) and sat NaHCO3 (2×) before being dried on Na2SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in hept) afforded the title compound as a white solid (6.0 g, 18.9 mmol, 31%). MS (ESI): m/z [M−H]− 317.0.

Provenance & Evidence