聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 3-(1-Methyl-4-piperidinyl)-1-[3-(trifluoromethyl)phenyl]-1H-indazole

HRID 867713

反应方程式

HRID 867713 反应方程式
[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

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 24758氢化钠HCID 678673-氟三氟甲苯HCID 178480237HCID 178480237，化合物

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂2 次

反应条件

温度
90 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-fd13768195974e9cbd4fe79b1f53cd19
来源数据集
uspto-grants-1988_10
专利号
US04775761

关联笔记

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