Sodium Dithionite → HCID 178507225, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-3-fluoro-4-nitro-1H-indazole and 6-bromo-4-nitro-1H-indazole (3:2) (187 mg) was dissolved in methanol (6 ml) and water (1.2 ml) and treated with sodium dithionate (519 mg). The solution was stirred for 2 h at 20° C. then left to stand for 3 days. This solution was then treated with sodium dithionite (438 mg) and stirred at 20° C. for 20 h. The solution was filtered through a filter tube, the residue washed with methanol (5 ml) then the combined filtrates were evaporated to dryness to give a yellow solid. This was treated with ethyl acetate (10 ml) and water (10 ml) and the solid dissolved. The organic phase was separated, dried with sodium sulphate, filtered then evaporated to give a pale yellow solid. This solid was treated with DCM (5 ml), methanol (5 ml) and ethyl acetate (10 ml), but some white solid did not dissolve. The supernatant was pipetted off, then blown to dryness to give a yellow solid which was dissolved in 1:1 methanol:DMSO (1 ml) and purified by mass directed preparative HPLC (Method A). The residue was azeotroped with methanol (5 ml) to give the title compound (19 mg) as a white solid.

Provenance & Evidence