Methyl iodide → HCID 58267997, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence