Sodium Iodide → HCID 59426223, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]-1-ethyl-6-hydroxy-1H-indole-3-carbonitrile, prepared in example 1AT above (70 mg, 0.25 mmol), K2CO3 (75 mg, 0.51 mmol), sodium iodide (27 mg, 0.18 mmol), 4-(2-chloroethyl) morpholine hydrochloride (42 mg, 0.25 mmol) in methyl ethyl ketone (3 mL) was heated in a sealed tube at 100° C. After 13 hours, DMF (3 mL) was added and the reaction was heated for an additional 6 h. After this time, an additional 42 mg of 4-(2-chloroethyl) morpholine hydrochloride and 135 mg of K2CO3 was added and the reaction was heated for an additional 6 h to complete the reaction. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (3×). The combined organic phases were washed with water (2×) and saturated NaCl and dried and concentrated. Pure 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-phenyl]-1-ethyl-6-(2-morpholin-4-yl-ethoxy)-1H-indole-3-carbonitrile was obtained by flash chromatography (MeOH/CH2Cl2, 0-6%) to give 29 mg (34%) of a tan solid.

Provenance & Evidence