Methyl iodide → 1-Methyl-5-nitro-1H-indazole

NaH (1.47 g, 36.8 mmol) was added to THF (40 mL) at 0° C. Separately, 5-nitroindazole (5.0 g, 30.6 mmol) was dissolved in THF (30 mL), and the mixed solution was slowly added to the prepared solution. Iodomethane (2.1 mL, 33.7 mmol) was added to the reaction solution at the same temperature, followed by stirring for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and added with water and ethyl acetate. The reaction mixture was added with distilled water for quenching, diluted with ethyl acetate, and washed with distilled water. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrated compound (1-methyl added (Rf=0.3), 2-methyl added (Rf=0.1)) was purified using silica gel chromatography (ethyl acetate:hexane=1:1 (v/v)) to obtain the title compound (Rf=0.3, 2.29 g, 42%).

1. additionthe mixed solution was slowly added to the prepared solution
2. concentrationThe reaction solution was concentrated under reduced pressure
3. additionadded with water and ethyl acetate
4. additionThe reaction mixture was added with distilled water
5. customfor quenching
6. additiondiluted with ethyl acetate
7. washwashed with distilled water
8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. additionThe concentrated compound (1-methyl added (Rf=0.3), 2-methyl added (Rf=0.1))
11. customwas purified

ORD-Eintrag

ord-d1f66e03f2c84699864a73b04b33168c

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09156852B2