N-bromobutanimide → HCID 69535222, compound

HRID 1006422Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Br:28]N1C(=O)CCC1=O>C1COCC1.C1CCCCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]([Br:28])=[CH:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -70 °C

Procedure

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).

Workup

stirringthe mixture was stirred at 0° C. for 0.5 hr
extractionextracted with 25 mL ether
washThe organic phase was washed with 5 mL water
dry with materialdried (magnesium sulfate)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-bd811f5041c3420aa924e4b6a32e93d3
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790848B2

Reaction notes

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