Methyl iodide → HCID 59276543, compound

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Reaction Steps

1,4-Dimethyl-6-nitro-1H-indazole. 4-Methyl-6-nitro-1H-indazole (0.75 g, 4.23 mmol) was dissolved in N,N-dimethylformamide (10 mL). Sodium hydride (0.203 g, 5.08 mmol, 60% dispersion in mineral oil) was then added at ambient temperature. After 15 minutes, methyl iodide (0.318 mL, 5.08 mmol) in N,N-dimethylformamide (0.5 mL) was added dropwise to the solution and allowed to stir at ambient temperature. After 2 h, LCMS analysis showed two peaks in the UV trace, both with the same product masses as geometric isomers. The solution was condensed under reduced pressure to give a brown solid. The solid was diluted with water (25 mL) and sonicated for 5 minutes. The resultant solid was filtered and washed with additional water followed by hexanes to afford a tan solid. The solid was purified via column chromatography (Biotage, eluting with 0-100% ethyl acetate in hexanes) to afford the title compound (0.480 g, 2.51 mmol, 59% yield) as verified via 1H NMR and NOE NMR. NOE-NMR (400 MHz, DMSO-d6) δ (ppm) 4.18 (Irradiate peak). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 8.55 (s, 1H), 8.35 (s, 1H), 7.77 (s, 1H), 4.18 (s, 3H), 2.66 (s, 3H); MS (ESI) m/z 192.4 [M+1]+.

Provenance & Evidence