Isopropanol → 6-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole

Participants

Reaction Conditions

Reaction Steps

6-Bromo-1-methyl-4-nitro-1H-indazole (100 mg, 0.39 mmol), Pd(dppf)Cl2 (32 mg, 0.04 mmol) and 1H-indol-4-ylboronic acid (94 mg, 0.59 mmol) were treated with a 4:1 mixture of propan-2-ol and saturated sodium bicarbonate solution (3 ml) and the reaction was heated in a microwave at 150° C. for 10 mins. Ethyl acetate was added, a solid was filtered off and the filtrate was partitioned between ethyl acetate and water. The water was washed twice with ethyl acetate and the combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica chromatography, eluting with 0-25% ethyl acetate in cyclohexane. Appropriate fractions were combined and evaporated to give the title compound (49 mg) as an orange solid.

Provenance & Evidence