4-Bromophenol → HCID 117675489, 화합물

HRID 1526185노트

반응식

HRID 1526185 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 117675489HCID 117675489, 화합물수율 88.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-388f575b9e4d4237994ecbec99ad5d7a
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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