Sulfuric acid magnesium salt (1:1) → HCID 53793030, compound

Participants

Reaction Steps

To a solution of 3-(2-aminoethyl)-2-(3,5-dichlorophenyl)-1H-indole-5-carboxylic acid ethyl ester (prepared essentially as described in Example 5.1, 100 mg in 7.0 mL chloroform) at -5° C. was added 172 mg of magnesium sulfate followed by 46.3 mg of 4-pyridin-3-yl-butyraldehyde and the mixture stirred at low temperature for 15 minutes. At this time, a solution of sodium borohydride (13.7 mg in 1.2 mL dry methanol) was added and after another 40 minutes, the reaction was quenched by the addition of water. The mixture was partitioned between ethyl acetate and saturated potassium carbonate, extracted and the organic portion washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 92:8) gave the title compound (100 mg).

Provenance & Evidence