Aluminium lithium hydride → 6-bromo-N-methyl-1H-indazol-3-amine

Temperature

100 °C

To a solution of phenyl 6-bromo-1H-indazol-3-ylcarbamate (0.80 g, 2.42 mmol) in 1,4-dioxane (40 mL) was added lithium aluminum hydride (2 M solution in THF, 2.42 mL, 2.42 mmol) dropwise at room temperature. After stirring at 100° C. for 4 hours, the reaction was quenched by 0.2 mL water, followed by 0.2 mL 15% NaOH and 0.6 mL water. The reaction mixture was then filtered and the solid was washed by ethyl acetate. The combined organic layer was washed by brine, dried with sodium sulfate and concentrated in vacuo. The crude residue was purified by flash chromatography with 50:50 (v/v) ethyl acetate-hexanes to afford the title product (0.29 g).

1. customthe reaction was quenched by 0.2 mL water
2. filtrationThe reaction mixture was then filtered
3. washthe solid was washed by ethyl acetate
4. washThe combined organic layer was washed by brine
5. dry with materialdried with sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by flash chromatography with 50:50 (v/v) ethyl acetate-hexanes

ORD record

ord-3214c2aceb914e65961dd9f0aea7100d

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987275B2