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 (60% in mineral oil) (62 mg) was then slowly added. The mixture was stirred for 15 min, then methyl iodide (221 mg) 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-6a380060594c4b668618abdd9ef2cc78

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326987B2