Lawesson's reagent → N5-(1-carbamothioylcyclopropyl)-6-chloro-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

Participants

Reaction Steps

6-Chloro-N5-(1-cyanocyclopropyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (0.200 g, 0.35 mmol) is initially charged in tetrahydrofuran (5.5 ml) under argon, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide (0.305 g, 0.75 mmol) is added and the mixture is stirred at room temperature for 48 h. Then 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide (0.150 g, 0.38 mmol) is added again and the mixture is stirred at room temperature for a further 12 h. The reaction mixture is then diluted with ethyl acetate and washed with a sodium hydrogencarbonate solution. The organic phase is dried with magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by means of preparative HPLC (Kromasil100, C18 250×20; eluent: acetonitrile in water, gradient: 10-100%) to obtain 0.025 g (11% of theory) of N5-(1-carbamothioylcyclopropyl)-6-chloro-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide.

Provenance & Evidence