Water → HCID 21894750, compound

Participants

Reaction Steps

Sodium hydride (80% suspension in oil, 0.7 g, 0.023 mol) was suspended in N,N-dimethylformamide (DMF) (10 ml) and then a solution of 5-bromoindazole (4.1 g, 0.021 mol) in DMF (40 ml) was added dropwise over 30 minutes. Once the addition was complete the mixture was stirred at ambient temperature for 75 minutes and then a solution of 1-bromo-2-methylpropane (3.7 g, 0.027 mol) in DMF (25 ml) was added over 10 minutes. The mixture was stirred for 5 hours and was then allowed to stand at ambient temperature overnight. The mixture was poured into water, extracted with diethyl ether and then the organic extract was washed further with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1:1 diethyl ether:hexane to give 5-bromo-1-(2-methylpropyl)indazole (2.67 g) and 5-bromo-2-(2-methylpropyl)indazole (1.49 g), each as an orange oil.

Provenance & Evidence