Methyl iodide → 3-iodo-5-isopropyl-1-methyl-1H-indazole

Temperature

0 °C

To a stirred solution of 3-iodo-5-isopropyl-1H-indazole (0.75 g, crude) in 50 mL of THF at 0° C. was added t-BuOK (0.59 g, 5.2 mmol) in one portion. The mixture was stirred at 0° C. for 30 minutes. CH3I (1.1 g, 7.7 mmol) was added and the solution was stirred at room temperature overnight. The reaction was quenched with 30 mL of water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL) and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated under reduced pressure to give crude 3-iodo-5-isopropyl-1-methyl-1H-indazole which contained some N-2 alkylation isomer (0.7 g) as oil. LCMS: (M+H)+=301.

1. stirringthe solution was stirred at room temperature overnight
2. customThe reaction was quenched with 30 mL of water
3. extractionextracted with ethyl acetate (2×100 mL)
4. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
5. dry with materialdried over anhydrous Na2SO4
6. customThe drying agent was removed by filtration
7. customthe filtrate was evaporated under reduced pressure

ORD record

ord-6e1bab67c6084627b907ad79e36336cb

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2