Hydrogen Peroxide → HCID 52933353, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid 4-methylsulfamoyl-benzylamide (0.1 g, 0.2 mmol), bis(pinacolato)diboron (0.1 g, 0.4 mmol), PdCl2(dppf) (0.04 g, 0.05 mmol), potassium acetate (0.05 g, 0.5 mmol) is charged in a sealed tube with anhydrous THF (7 mL). The solution is warmed at 80° C. for 16 hours. The reaction mixture is cooled to room temperature and quenched with water (15 mL) and diluted with CH2Cl2 (20 mL). The organic layer is separated and washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue is dissolved in THF (10 mL), and a solution of 30% H2O2 in water (0.15 mL, 0.5 mmol) and NaOH (0.01 g, 0.3 mmol) is added. The mixture is stirred at 10° C. for 3 hours and is then quenched with water (10 mL) and diluted with CH2Cl2 (20 mL). The organic layer is washed with brine (10 mL) and dried over sodium sulfate and concentrated in vacuo. The residue is purified by reversed-phase HPLC eluting with a gradient of 5-100% CH3CN in water. The desired fractions are combined and diluted with saturated aqueous NaHCO3 (20 mL) and EtOAc (20 mL). The organic layer is separated, dried over sodium sulfate and concentrated to afford the title compound.

Provenance & Evidence