Dichloromethane → HCID 25070421, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-bromobenzenesulfonamide (50 mg, 0.21 mmol), bis(pinacolato)diboron (54 mg, 0.21 mmol), potassium acetate (78 mg, 0.80 mmol) and Pd(dppf)Cl2.DCM (9 mg, 0.0105 mmol) in anhydrous dimethylformamide (1 mL) was degassed under argon for 10 minutes and then stirred at 80° C. for 2 h. The reaction mixture was allowed to cool to room temperature and 3-{[1-iodo-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol (46 mg, 0.105 mmol), an aqueous solution of sodium carbonate 2M (367 μL, 0.735 mmol) and Pd(PPh3)4 (5 mg, 0.0042 mmol) was added. The mixture was stirred under argon at 80° C. overnight and then cooled to room temperature, diluted with cold water and extracted four times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 90/10) to afford 3-{4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-1-yl}benzenesulfonamide (14 mg, 28%) as a white solid.

Provenance & Evidence