N-bromobutanimide → HCID 66681584, compound

HRID 1964506Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[S:14][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>O1CCCC1>[Br:23][C:12]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]([C:13]2[S:14][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:17]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 2-[1-(t-butoxycarbonyl)-1H-pyrrol-2-yl]-1,3-thiazole-5-carboxylate (800 mg, 2.48 mmol) synthesized in Example (5a) was dissolved in tetrahydrofuran (30 mL), and cooled to 0° C. N-Bromosuccinimide (442 mg, 2.48 mmol) was added with stirring under nitrogen atmosphere, and subsequently stirring was carried out at room temperature for 19 hours. A saturated aqueous sodium hydrogencarbonate solution (30 mL) was added, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%) to afford the desired compound (598 mg, yield 60%) as a pale yellow solid.

Workup

stirringsubsequently stirring
extractionextraction
washThe organic layer was washed with saturated brine
dry with materialsubsequently dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified
washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%)

Sources & evidence

ORD record: ord-479be7f1b7374e8cb7c242835297d652
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415359B2

Reaction notes

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