4-Bromophenol → HCID 117675489, compound

HRID 1526185Notes

Reaction equation

HRID 1526185 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:26][CH3:27])[C:7]([O:11][C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=2)=[N:8][C:9]=1Cl)(=[O:3])[NH2:2].[Br:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][C:9]2[N:8]=[C:7]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=3)[C:6]([CH2:26][CH3:27])=[N:5][C:4]=2[C:1](=[O:3])[NH2:2])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 117675499HCID 117675499, compound

Product 1

HCID 117675489HCID 117675489, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl {3-[(5-carbamoyl-6-chloro-3-ethylpyrazin-2-yl)oxy]phenyl}carbamate (500 mg), 4-bromophenol (440 mg), potassium carbonate (440 mg), and N-methylpyrrolidone (5 mL) was reacted at 100° C. for 4 hours. The reaction mixture was left to be cooled, and then water-saturated brine (1:1) was added thereto, followed by extraction with ethyl acetate. Then, the organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-95:5, hexane:ethyl acetate=7:3-3:7) to obtain tert-butyl (3-{[6-(4-bromophenoxy)-5-carbamoyl-3-ethylpyrazin-2-yl]oxy}phenyl)carbamate (599 mg) as a colorless solid.

Workup

  1. customwas reacted at 100° C. for 4 hours
  2. waitThe reaction mixture was left
  3. temperatureto be cooled
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThen, the organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-95:5, hexane:ethyl acetate=7:3-3:7)

Sources & evidence

ORD record
ord-388f575b9e4d4237994ecbec99ad5d7a
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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