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

HRID 1166356

反応式

HRID 1166356 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[NH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29]>C(O)(C)C>[OH:32][C:27]1([C:28]([F:31])([F:30])[F:29])[CH2:26][N:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:13]1

参加物

5

反応物 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178504797HCID 178504797、化合物

生成物 1

HCID 229979882-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine収率 18%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
77.5 °C

実験手順

To a mixture of the amidine of step 1 (4.4 g, 16 mmol) and sodium bicarbonate (2.7 g, 32 mmol) in isopropanol (400 ml), 3-bromo-1,1,1-trifluoroacetone (2.5 ml, 24 mmol) was added. After heating at 75-80° C. for 24 hours, the reaction mixture was cooled and filtered. The residue was washed with methylene chloride and the combined organic fractions were dried over sodium sulfate, filtered and concentrated. The crude product (16.2 g) was purified by chromatography (silica gel, ethyl acetate/toluene 1/1) to give 2-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine (1.1 g, 18%) as a white solid: mp 195-198° C. Anal. Calc'd. for C16H14N3SO3F3: C, 49.87, H, 3.66, N, 10.90. Found: C, 50.13, H, 3.66, N, 10.30.

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe residue was washed with methylene chloride
  5. dry with materialthe combined organic fractions were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product (16.2 g) was purified by chromatography (silica gel, ethyl acetate/toluene 1/1)

出典と根拠

ORDレコード
ord-c8412f9c37364d1bb9972e301cd154c8
出典データセット
uspto-grants-2003_09
特許番号
US06613789B2

関連ノート

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