N-bromobutanimide → HCID 69535222, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of 0.4 g (1.32 mmole) 4-(1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester in 10 mL THF was added 0.83 mL (1.65 mmole) 2M n-butyl lithium in cyclohexane. The reaction mixture was stirred for 5 min and then cooled to −70° C. A solution of 0.26 g (1.44 mmole) N-bromosuccinimide in 6 mL THF was added and the mixture was stirred at 0° C. for 0.5 hr. The mixture was diluted with 10 mL water and extracted with 25 mL ether. The organic phase was washed with 5 mL water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to column chromatography over silica gel eluting with hexane/chloroform/ethyl acetate (50:48:2) to afford) 4-(3-bromo-1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as a foam, 0.46 g. Nmr (deuteriochloroform) ppm δ: 1.50 (s 9H), 3.08 (m, 4H), 3.71 (m, 4H), 6.72 (dd, 1H), 7.14 (m, 3H), 8.42 (brs, 1H).

Provenance & Evidence