1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl 2-(6-(3-chloro-1H-indole-2-carboxamido)-1H-indol-1-yl)acetate

DIPEA (2.5 equiv.), EDCI (2.73 mmol, 1.2 equiv.) and HOBt (2.73 mmol, 1.2 equiv.) were added at 0° C. to a solution of 3-chloro-1H-indole-2-carboxylic acid (2.27 mmol, 1.0 equiv.) in DMF (6 ml), and the mixture was stirred for 15 min. tert-Butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A—for synthesis see above) (2.27 mmol, 1.0 equiv.) was dissolved in DMF (1 ml) and added, with stirring, and the reaction mixture was then stirred for 12 h at 25° C. The mixture was diluted with dichloromethane (50 ml), washed with sat. ammonium chloride solution (20 ml), water (20 ml) and sat. NaCl solution (20 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (10-15% ethyl acetate in hexane). Yield: 55%

1. additionadded
2. stirringthe reaction mixture was then stirred for 12 h at 25° C
3. washwashed with sat. ammonium chloride solution (20 ml), water (20 ml) and sat. NaCl solution (20 ml)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by column chromatography (10-15% ethyl acetate in hexane)

ORD record

ord-d0a7d4753e7941c2939065ded2696b55

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492559B2