3-Bromo-1,1,1-trifluoro-2-propanone → 3-methyl-6-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

HRID 52351ノート

反応式

HRID 52351 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].Br[CH2:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30]>C(O)(C)C>[CH3:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)[CH2:27][C:28]([OH:33])([C:29]([F:32])([F:31])[F:30])[N:20]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178425635HCID 178425635、化合物

生成物 1

HCID 199633603-methyl-6-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a mixture of the amidine of step 1 (10 mmol and sodium bicarbonate (20 mmol) in isopropanol (150 ml), 3-bromo-1,1,1-trifluoroacetone (15 mmol) is added. After heating at 80°-85° C. for 24 hours, the reaction mixture is cooled and filtered. The residue is washed with methylene chloride and the combined organic fractions are dried over sodium sulfate, filtered and concentrated. The crude mixture is chromatographed on silica gel using mixtures of ethyl acetate, isopropanol and ammonium hydroxide as eluants to give the desired 4,5-dihydro-imidazole

後処理

  1. additionis added
  2. temperatureAfter heating at 80°-85° C. for 24 hours
  3. temperaturethe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe residue is washed with methylene chloride
  6. dry with materialthe combined organic fractions are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture is chromatographed on silica gel using mixtures of ethyl acetate, isopropanol and ammonium hydroxide as eluants

出典と根拠

ORDレコード
ord-316ba6187fd74b6abe45e83fcd3d544a
出典データセット
uspto-grants-1997_04
特許番号
US05616601

反応ノート

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