Triethylamine → 2-(5-bromo-1H-indol-3-yl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

The method of Bascop, S. I.; Laronze, J. Y.; Sapi, J. Synthetis of 2-aminopropyle-3-indole-acetic(propionic) acid derivatives. ARKIVOC 2003, 46-61, was followed. Methane sulphonyl chloride (MsCl, 0.55 mL, 2 equiv) was added to a stirred solution of 13 (3.2 mmol, 1 equiv), triethylamine (0.9 mL, 2 equiv) and anhydrous CH2Cl2 (20 mL) maintained at 0° C. The reaction mixture was then stirred for 30 min at 0° C. under N2, after which it was treated with 2M NaOH and extracted with CH2Cl2. The combined organic layer was washed with water, dried (anhydrous Na2SO4) and evaporated to dryness under reduced pressure. The residue was dissolved in anhydrous DMSO (20 mL), KCN (3.25 mmol, 3 equiv) was added and the reaction mixture was heated at 100° C. in an oil bath for 1 h. It was diluted with a water-ice mixture, extracted with chloroform, the combined organic layer was washed with water, dried (anhydrous Na2SO4), and evaporated to dryness under reduced pressure. The residue was purified by column chromatography with CHCl3 as eluting solvent and 14 was obtained. Yield: 75%; 1H NMR (300 MHz, DMSO-d6): δ 2.78 (t, J=15 Hz, 2 H), 3.58 (t, J=12 Hz, 2 H), 7.14-7.17 (m, 2 H), 7.20 (d, J=27 Hz, 1 H), 7.68 (s, 1 H), 11.01 (s, 1 H); MS (APCI): m/z 261.3 [M+H]+.

Provenance & Evidence