Methyl iodide → 3-Iodo-1-methyl-1H-indazole-6-carbonitrile

Participants

Reaction Steps

To a suspension of 3-iodo-1H-indazole-6-carbonitrile (2.0 g, 7.43 mmol), t-BuOK (1.2 g, 10.4 mmol) in THF (50 mL), iodomethane (1.2 g, 10.4 mmol) in THF (5 mL) was added dropwise at 0° C. under ice-water bath. The resulting mixture was stirred overnight at room temperature. Two isomers, which are methylated at N-1 and N-2 position respectively, were formed. The excess solvent was removed under reduced pressure, the residue was dissolved in EtOAc (100 mL), washed with brine (2×10 mL), the combined organics were dried over Na2SO4. After removal of drying agent and concentration, the crude mixture (1.6 g) was used in the next step without further purification. MS: (M+H)+=411;

Provenance & Evidence