Potassium Carbonate → 3-iodo-1-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole

To (1-methyl-1H-pyrazol-3-yl)methanol (2.01 g, 17.93 mmol) in DCM (80 mL) at 0° C. was cautiously added thionyl chloride (10.43 mL, 143.4 mmol). The cold bath was removed and the reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The residual yellow solid was diluted with DMF (30 mL). 3-Iodo-4-nitro-1H-indazole (5.181 g, 17.93 mmol) and K2CO3 (7.432 g, 53.78 mmol) were added to the DMF solution. The reaction mixture was stirred for 20 hours, and concentrated under reduced pressure to remove most of the DMF. The residue was diluted with DCM (100 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/Hexane 1:3) to provide the product (5.11 g).

1. customat 0° C.
2. customThe cold bath was removed
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additionThe residual yellow solid was diluted with DMF (30 mL)
5. stirringThe reaction mixture was stirred for 20 hours
6. concentrationconcentrated under reduced pressure
7. customto remove most of the DMF
8. additionThe residue was diluted with DCM (100 mL)
9. washwashed with H2O
10. dry with materialThe organic phase was dried (Na2SO4)
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel chromatography (EtOAc/Hexane 1:3)

ORD-Eintrag

ord-633e65df7b164fa2b174d505f013a6e6

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841455B2