Water → t-Butyl 2-bromo-5-(5-methylpyrazin-2-yl)-1H-pyrrole-1-carboxylate

HRID 1964516Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

t-Butyl 2-(5-methylpyrazin-2-yl)-1H-pyrrole-1-carboxylate (373 mg, 1.44 mmol) synthesized in Example (10a) was dissolved in tetrahydrofuran (20 mL), and cooled to 0° C. N-Bromosuccinimide (256 mg, 1.44 mmol) was added, and stirring was carried out at room temperature for 14 hours under nitrogen atmosphere. Water (20 mL) was added, and extraction was carried out with diethyl ether (20 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 (425 mg, yield 87%) as a pale yellow oil.

Workup

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-59a75f2eabe1495fa94e826c887619e1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415359B2

Reaction notes

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