1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1,2-dimethyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Participants

Reaction Steps

To a stirred solution of 1,2-dimethyl-3-(methylaminomethyl)-1H-indol e (0.8 g, 4.2 mmole) in 1:1 DMF/CH2Cy2 (30 mL) at RT was added (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.7 g, 4.3 mmole), Et3N (0.61 ml, 4.3 mmole), HOBt H2O (0.58 g, 4.3 mmole) and EDC (0.83 g, 4.3 mmole). After 16 h the reaction was concentrated under vacuum and the residue was taken up in EtOAc (100 mL). The solution was washed with 1.0 N Na2CO3 (100 mL) then with brine, dried (Na2SO4), and concentrated. Purification by flas h chromatography on silica gel (4% MeOv.CHCl3) followed by trituration with 1:1 Et2O/petroleum ether and drying under vacuum gave (he title compound (1.36 g, 97%) as an off-white solid: MS (ES) H+e 335.2 (M+H)+.

Provenance & Evidence