Triethylborane → 4-[2-(6-Methyl-pyridin-2-yl)-4-trifluoromethyl-imidazol-1-yl]-benzenesulfonamide

HRID 1352987노트

반응식

HRID 1352987 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23](C)(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[N:3]=1.C([Mg]Cl)CCC.C(B(CC)CC)C.C([O-])(=O)C.[Na+].[NH2:45]OS(O)(=O)=O>O1CCCC1.O>[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH2:45])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 7357TriethylboraneHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 10293184Pyridine,2-methyl-6-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1h-imidazol-2-yl]-HCID 178418265HCID 178418265, 화합물

생성물 1

HCID 102712314-[2-(6-Methyl-pyridin-2-yl)-4-trifluoromethyl-imidazol-1-yl]-benzenesulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a clear solution of Example 32 (10 mmol) in tetrahydrofuran (60 ml) at 0° C., n-BuMgCl (2M solution in THF, 25 ml, 50 mmol) is added over 10 minutes. After stirring for an additional 20 minutes, the ice bath is removed and the solution is stirred for 2 hours. The reaction mixture is recooled to 0° C. and triethylborane (1M solution in THF, 60 ml, 60 mmol) is added. After stirring for 1 hour, the reaction is heated to reflux for 72 hours. The reaction mixture is cooled to room temperature and treated with aqueous sodium acetate (5.5 g in 22 ml water). After stirring for 5 minutes, solid hydroxylamine-O-sulfonic acid (5.5 g) is added and the mixture stirred for 24 hours. The reaction mixture is diluted with water and extracted with ether. The ethereal layer is dried over sodium sulfate, filtered and concentrated. The crude solid is purified by chromatography on silica gel using mixtures of hexane and isopropanol to give the desired product.

후처리

  1. customthe ice bath is removed
  2. stirringthe solution is stirred for 2 hours
  3. customis recooled to 0° C.
  4. stirringAfter stirring for 1 hour
  5. temperaturethe reaction is heated
  6. temperatureto reflux for 72 hours
  7. stirringAfter stirring for 5 minutes
  8. stirringthe mixture stirred for 24 hours
  9. extractionextracted with ether
  10. dry with materialThe ethereal layer is dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude solid is purified by chromatography on silica gel using mixtures of hexane and isopropanol

출처 및 근거

ORD 기록
ord-fd0777532e794b36ad50d3dd53393282
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220770B2

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