Phenol → 1-{2-[1-(8-Methyl-2,3-dihydro-[1,4]-dioxino[2,3-f]quinolin-2-ylmethyl)-azetidin-3-yl]-ethyl}-1h-indole-6-carbonitrile

Beteiligte Stoffe

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Reaktionsschritte

A solution of (2R)-4-bromobenzenesulfonic acid 8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester (0.21 g, 0.45 mmol) 1-(2-azetidin-3-yl-ethyl)-1H-indole-6-carbonitrile (0.11 g, 0.52 mmol), which was made in two steps from 6-cyanoindole according to the procedures described for Intermediates 40 and 41, and triethylamine (0.14 ml, 1 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 (10% methanol-ethyl acetate). The product-containing fractions were concentrated in vacuum to give 0.08 g of the (S)-enantiomer of the title compound as a brown oil. The hydrochloride salt was prepared in ethyl acetate and collected as a yellow solid: yellow solid, m.p. 144° C. (dec).

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