N-(2-INDOL-3-YLETHYL)(4-METHYLPHENYL)FORMAMIDE synthesis

Yield:881597-49-5 92%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 1 h;Inert atmosphere;

Steps:

3.4.1. General Procedure for Synthesis of Compounds 14-21 by Reaction of Commercially AvailableAcyl Chlorides with Tryptamine (Procedure A)

General procedure: To the solution of tryptamine (1, 1.87 mM) in dry CH2Cl2 (8 mL), that had been pre-cooled to 0 C,the Et3N (3.74 mM) and acyl chloride (2-9, 2.43 mM) were gradually added. The resulting mixturewas stirred for 10 min at 0 C and then at room temperature for a further 50 min. The course ofreactions was monitored by TLC. Subsequently the solvent was evaporated under vacuum and theresidue was chromatographed on silica gel, eluent heptane-EtOAc (1:1) (for compounds 14-16) andheptane-EtOAc (2:1) (for compounds 17-21).

References:

Honegr, Jan;Dolezal, Rafael;Malinak, David;Benkova, Marketa;Soukup, Ondrej;De Almeida, Joyce S. F. D.;Franca, Tanos C. C.;Kuca, Kamil;Prymula, Roman [Molecules,2018,vol. 23,# 1,art. no. 102]