HCID 10269137, compound → HCID 60037060, compound

Participants

Reaction Steps

5-(3-Dimethylamino-prop-1-ynyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.160 g, 0.428 mmol, 1 eq, Example 53) was dissolved in ethanol (30 mL). Lindlar's catalyst (0.05 mg) was added, and the reaction was hydrogenated at room temperature under a hydrogen atmosphere, 35 PSI. The reaction mixture was shaken at room temperature and followed by LC-MS. After one week, the reaction was loaded on silica gel and chromatographed, (ethyl acetate/methanol/triethylamine 87/10/3). The resulting indole-alkene product (0.019 g, 12%) was converted to the —HCl salt, obtained as a brown semisolid: LC/MS (ESI+) 377 (M+1), Anal. (C24H28N2O2.HCl.1.0H2O) C, H, N.

Provenance & Evidence