Water → 3-(1-Methyl-4-piperidinyl)-1-[3-(trifluoromethyl)phenyl]-1H-indazole

HRID 867713

反応式

HRID 867713 の反応式
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.F[C:20]1[CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1.O>CN(C)C=O>[CH3:3][N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[N:11]=2)[CH2:8][CH2:9]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67867alpha,alpha,alpha,3-TetrafluorotolueneHCID 178480237HCID 178480237、化合物

生成物 1

HCID 140325833-(1-Methyl-4-piperidinyl)-1-[3-(trifluoromethyl)phenyl]-1H-indazole収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
90 °C

実験手順

To a stirred suspension of 4.9 g of a 50% oil dispersion of sodium hydride in 60 ml of dimethylformamide was added dropwise a solution a 10.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 80 ml of hot dimethylformamide. The reaction mixture was stirred for 1 hr and then 15.2 g of 3-fluorobenzotrifluoride was added. The reaction was heated at 90° C. for 22 hrs, cooled and poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was flash chromatographed (silica gel, diethylamine-ethyl acetate (1:9)). Evaporation of the appropriate fractions followed by recrystallization twice from hexane yielded 2.96 g (18%) of product, mp 103°-105° C.

後処理

  1. temperaturecooled
  2. extractionThe aqueous mixture was extracted with ether
  3. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil
  6. customchromatographed (silica gel, diethylamine-ethyl acetate (1:9))
  7. customEvaporation of the appropriate fractions
  8. customfollowed by recrystallization twice from hexane

出典と根拠

ORDレコード
ord-fd13768195974e9cbd4fe79b1f53cd19
出典データセット
uspto-grants-1988_10
特許番号
US04775761

関連ノート

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