Methyl iodide → HCID 67540656, compound

Participants

Reaction Steps

To a stirred suspension of NaH (60%, 4 mg, 0.1 mmol) in DMF (0.5 mL) was added dropwise a solution of 4-(1H-Indazol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.100 g, 0.33 mmol) in DMF (1 mL). After stirring for 30 minutes, methyl iodide (0.026 g, 0.18 mmol) was added dropwise. The mixture was stirred at room temperature for 2 hours and then partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (hexanes:EtOAc, 2:1) to give 4-(1-Methyl-1H-indazol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.023 g, 22%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.87 (s, 1H), 7.32 (d, J=9.2 Hz, 1H), 7.20 (d, J=9.2 Hz, 1H), 7.12 (s, 1H), 4.04 (s, 3H), 3.62 (m, 4H), 3.09 (m, 4H), 1.50 (s, 9H). LCMS (APCI+) m/z 317 [M+H]+; Rt=3.31 minutes.

Provenance & Evidence