Benzyl Bromide → HCID 178434287, compound

Participants

Reaction Steps

To a suspension of sodium hydride (0.452 g of a 60% dispersion in mineral oil, 11.3 mmol) in DMF (30 mL) was added 4-hydroxy-3-methylindazole (1.52 g, 10.3 mmol) (prepared in a similar manner to that described in J. Med Chem., 2000, 2672) in DMF (20 mL) via a cannula. The mixture was stirred at room temperature for 10 minutes and then benzyl bromide (1.223 mL, 10.3 mmol) was added and stirring was continued at room temperature for 2 hrs. The mixture was quenched with ammonium chloride solution and the DMF was evaporated. Ethyl acetate and water were added and the product was extracted into ethyl acetate and the extracts were dried (Na2SO4) and evaporated. Chromatography (0-100% ethyl acetate in hexane) gave the title compound (D30) as an orange solid (1.774 g, containing ˜10% dibenzylated material).

Provenance & Evidence