Dimethyl Sulfoxide → N-[3-(4-amino-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide

온도

110 °C

N-[3-(4-Bromo-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide (0.5 g, 1.1 mmol) was taken in a reaction vial, followed by addition of sodium azide (0.286 g, 4.4 mmol), cuprous iodide (0.063 g, 0.3 mmol), N,N′-dimethylethane-1,2-diamine (0.058 g, 0.6 mmol) and dimethylsulfoxide (12 mL). The vial was sealed properly and heated at 110° C. for overnight. The reaction mixture was cooled to room temperature and water (100 mL) was added, extracted with ethyl acetate (3×150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by silica gel (100-200 mesh) column chromatography using 2% methanol in dichloromethane to afford pure N-[3-(4-amino-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide (0.23 g, 47%).

1. customThe vial was sealed properly
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionextracted with ethyl acetate (3×150 mL)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum
6. customThe crude product was purified by silica gel (100-200 mesh) column chromatography

ORD 기록

ord-3f54c0a7b0f24be5955a05c196542699

출처 데이터셋

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09364466B2