Water → 3-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine

온도

80 °C

To a solution of 5-(difluoromethoxy)-3-iodo-1H-indazole (1 g, 3.2 mmol) in DMF (25 mL) was added K2CO3 (1.8 g, 12.8 mmol) and 3-chloro-N,N-dimethylpropan-1-amine (1.1 g, 6.4 mmol), after the addition, the reaction mixture was stirred at 80° C. for 4 hour. After cooling to room temperature, H2O (25 mL) was added and product extracted with ethyl acetate (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure, the residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with dichloromethane/CH3OH=10:1) to give 3-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (1.1 g, 78.5%) as yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.46-7.42 (m, 1H), 7.27-7.17 (m, 2H), 6.87-6.29 (t, 1H, J=73.8 Hz), 4.47-4.41 (m, 2H), 2.24-2.18 (m, 8H), 2.08-2.03 (m, 2H). LCMS: (M+H)+=396.

1. additionafter the addition
2. temperatureAfter cooling to room temperature
3. extractionproduct extracted with ethyl acetate (100 mL)
4. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customthe residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with dichloromethane/CH3OH=10:1)

ORD 기록

ord-e04eea713074407a9aa54e2b01a1b2be

출처 데이터셋

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08658646B2