Sodium Carbonate → N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-2-[1-(phenylsulfonyl)-1H-indol-3-yl]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

After purging a solution of 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide (595 mg; 1.42 mmol) in 14 ml of toluene and 12 ml of EtOH with argon for 20 minutes, the title product of Step (C) (600 mg; 1.99 mmol) was added followed by 2M Na2CO3 (10 ml; previously purged with argon) and tetrakis(triphenylphosphine)palladium(0) (200 mg). The heterogeneous mixture was heated to 75-80° C. for 5 hrs. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (50 ml) and water (25 ml). The aqueous layer was extracted with an additional 25 ml of ethyl acetate and the combined organic layers were washed with water (25 ml) and brine (25 ml). After drying (MgSO4) and decolorizing (Darco), the green solution was concentrated to afford a dark green residue which was chromatographed on a 5×12 cm silica gel column, using 2 L EtOAc:hexanes, 1:3, 1 L EtOAc:hexanes, 3:7 and 1 L EtOAc:hexanes, 35:65 as the mobile phase. The pure fractions were concentrated to afford 379 mg (45%) of the title product of this step as a blue-green foam.

Provenance & Evidence