反应详情

33.3 mg of α-toluene sulfonamide (0.0002M, 1.2 eq.) was dissolved in 0.5 mL of DMF and added to a slurry of 8.0 mg of 60% sodium hydride (0.0002M, 1.2 eq.) in 0.5 mL of DMF. The reaction was stirred for 30 min. at which point 100 mg of 4-{2-[1-Benzhydryl-2-(3-bromo-propyl)-5-chloro-1H-indol-3-yl]-ethoxy}-benzoic acid methyl ester (0.0002M, 1.0 eq.) in 0.5 mL of DMF was added and the solution was stirred for an additional 1 hour. The reaction was quenched with water and diluted with 10 mL of ethyl acetate. The organic layer was washed with water (2×5 mL) and brine (2×5 mL), dried over magnesium sulfate and evaporated to a yellow oil. The residue was purified via column chromatography (ethyl acetate/hexanes 5:95) to give 20 mg (17%) of 4-{2-[1-Benzhydryl-5-chloro-2-(3-phenylmethanesulfonylamino-propyl)-1H-indol-3-yl]-ethoxy}-benzoic acid methyl ester as a clear oil.

1. additionwas added
2. stirringthe solution was stirred for an additional 1 hour
3. customThe reaction was quenched with water
4. additiondiluted with 10 mL of ethyl acetate
5. washThe organic layer was washed with water (2×5 mL) and brine (2×5 mL)
6. dry with materialdried over magnesium sulfate
7. customevaporated to a yellow oil
8. customThe residue was purified via column chromatography (ethyl acetate/hexanes 5:95)