1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl 2-(5-(3-chloro-1H-pyrrole-2-carboxamido)-1H-indol-1-yl)acetate

온도

25 °C

DIPEA (4.0 equiv.), EDCI (1.5 equiv.) and HOBt (1.0 equiv.) were added at 0° C. to a solution of 3-chloro-1H-pyrrole-2-carboxylic acid (5.24 mmol, 1.0 equiv.) in DCM (25 ml). The mixture was stirred for 15 min at 25° C. and then cooled to 0° C. again. A solution of tert-butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A—for synthesis see above) (5.24 mmol, 1.0 equiv.) in DCM (10 ml) was added, and the reaction mixture was stirred for 16 h at 25° C. It was then diluted with DCM (200 ml), washed with sat. ammonium chloride solution (2×50 ml), sat. sodium hydrogen carbonate solution (2×50 ml) and sat. NaCl solution (2×50 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (6% methanol in DCM). Yield: 56%

1. temperaturecooled to 0° C. again
2. stirringthe reaction mixture was stirred for 16 h at 25° C
3. washwashed with sat. ammonium chloride solution (2×50 ml), sat. sodium hydrogen carbonate solution (2×50 ml) and sat. NaCl solution (2×50 ml)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by column chromatography (6% methanol in DCM)

ORD 기록

ord-aa54ab38478940a6b956c07f1e2d7cd8

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08492559B2