Methyl iodide → HCID 58267997, compound

Temperature

0 °C

6-Bromo-4-nitro-1H-indazole (available from Sinova, 1.05 g, 4.13 mmol) was dissolved in THF (20 ml) and cooled to 0° C. under nitrogen. 60% Sodium hydride in mineral oil (191 mg, 7.57 mmol) was added portion-wise allowing the evolution of gas to subside before adding the next portion. This was left under nitrogen, stirring at 0° C. for 15 mins. Iodomethane (0.298 ml, 4.78 mmol) in THF (5 ml) was added dropwise to the reaction, washing through with further THF (5 ml). The reaction was then allowed to warm to room temperature. The reaction was stirred for 5 h then partitioned between ethyl acetate and water, washing the water with ethyl acetate (x3). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was purified by silica chromatography using a gradient of 0-25% ethyl acetate in cyclohexane, to give the title compound (388 mg).

1. additionbefore adding the next portion
2. waitThis was left under nitrogen
3. washwashing through with further THF (5 ml)
4. temperatureto warm to room temperature
5. stirringThe reaction was stirred for 5 h
6. customthen partitioned between ethyl acetate and water
7. washwashing the water with ethyl acetate (x3)
8. washThe combined organics were washed with brine
9. dry with materialdried over magnesium sulphate
10. filtrationfiltered
11. customevaporated to dryness
12. customThe residue was purified by silica chromatography

ORD record

ord-8a04f0935a4d4690a4743577c643500c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765743B2