N-bromobutanimide → t-Butyl 2-bromo-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

HRID 909421Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

t-Butyl 2-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (6.70 g, 26.8 mmol) synthesized in Example (1f) was dissolved in tetrahydrofuran (100 mL) and cooled to 0° C. With stirring under nitrogen atmosphere, N-bromosuccinimide (4.79 g, 26.9 mmol) was divided into 5 parts to be added every 10 minutes, followed by further stirring at 0° C. for 2 hours. A saturated aqueous sodium hydrogencarbonate solution (200 mL) was added, and extraction was carried out with ethyl acetate (300 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium 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%-16%) to afford the desired compound (7.55 g, yield 86%) as a white solid.

Workup

additionto be added every 10 minutes
stirringby further stirring at 0° C. for 2 hours
extractionextraction
washThe organic layer was washed with saturated brine
dry with materialsubsequently dried over sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified
washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-16%)

Sources & evidence

ORD record: ord-94cb0de1ec5943119851089d71ebaae9
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017610B2

Reaction notes

Loading…