Methyl iodide → HCID 58255771, compound

Temperature

0 °C

6-Bromo-1H-indazol-4-amine (available from Sinova, 300 mg, 1.42 mmol) was dissolved in THF (7.5 ml) and the mixture cooled to 0° C. Sodium hydride (62 mg, 1.56 mmol) was then slowly added. The mixture was stirred for 15 minutes, then methyl iodide (221 mg, 1.56 mmol) was added and stirring continued at 0° C. for 3 h. The reaction mixture was quenched by careful addition of methanol (2 ml), then water (10 ml), then extracted into ethyl acetate and the organic layer was concentrated in vacuo. The residue was purified by column chromatography on silica eluting with a gradient of 0-50% ethyl acetate in cyclohexane. Fractions containing desired product were combined and concentrated in vacuo to afford the title compound (48 mg).

1. stirringstirring
2. waitcontinued at 0° C. for 3 h
3. customThe reaction mixture was quenched by careful addition of methanol (2 ml)
4. extractionwater (10 ml), then extracted into ethyl acetate
5. concentrationthe organic layer was concentrated in vacuo
6. customThe residue was purified by column chromatography on silica eluting with a gradient of 0-50% ethyl acetate in cyclohexane
7. additionFractions containing desired product
8. concentrationconcentrated in vacuo

ORD record

ord-a1a9f4dd1b714b83b443f4d75b7fa89a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765743B2