反应详情

A solution of (2R)-4-bromobenzenesulfonic acid 8-methyl-2,3-dihydro-[1,4]dioxino[2,3-]quinolin-2-ylmethyl ester (0.4 g, 0.93 mmol), 1-azetidin-3-ylmethyl-6-fluoro-1H-indole (0.19 g, 0.93 mmol) and triethylamine (0.19 ml, 1.4 mmol) in dimethylsulfoxide (20 ml) was heated at 90° C. under nitrogen overnight. The reaction mixture was quenched with 1N sodium hydroxide and extracted with methylene chloride (3×80 mL). The organic layer was washed with water (3×50 mL), dried over anhydrous sodium sulfate, filtered and the solvent removed under vacuum. The crude oil was column chromatographed on silica gel (3% methanol-ethyl acetate). The product-containing fractions were concentrated in vacuum to give 0.1 g of the (S)-enantiomer of the title compound as a brown oil. The hydrogen chloride salt was prepared in ethyl acetate and collected as a yellow solid: mp: 138° C. (dec).

1. customThe reaction mixture was quenched with 1N sodium hydroxide
2. extractionextracted with methylene chloride (3×80 mL)
3. washThe organic layer was washed with water (3×50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customthe solvent removed under vacuum
7. customchromatographed on silica gel (3% methanol-ethyl acetate)
8. concentrationThe product-containing fractions were concentrated in vacuum