1,2-二氯乙烷 → (R,E)-3-(1H-indol-3-yl)-N-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acrylamide

HRID 511861

反应方程式

HRID 511861 反应方程式
Cl.Cl.[F:3][C:4]([F:17])([F:16])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]([NH2:15])[CH3:14])=[N:11][CH:12]=1.C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.[CH2:25](Cl)[CH2:26]Cl.C1C=[CH:31][C:32]2N(O)N=N[C:33]=2[CH:34]=1.[C:39](=[O:42])(O)[O-].[Na+]>ClCCl>[NH:20]1[C:21]2[C:22](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24](/[CH:25]=[CH:26]/[C:39]([NH:15][C@@H:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([F:3])([F:16])[F:17])=[CH:12][N:11]=2)[CH3:14])=[O:42])=[CH:23]1

参与物

7

反应物 5

HCID 111,2-二氯乙烷HCID 8471三乙胺HCID 757711-羟基苯并三唑(HOBT)HCID 516892碳酸氢钠HCID 66892447(1R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethan-1-amine dihydrochloride

产物 1

HCID 67290429(R,E)-3-(1H-indol-3-yl)-N-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acrylamide收率 53%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

To a suspension of (R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethanamine 2HCl salt (1.1 g, 3.8 mmol) and (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yDacrylic acid (1.0 g, 3.5 mmol) in dichloromethane (8 mL) were added triethylamine (1.8 g, 17 mmol), EDC (800 mg, 4.2 mmol) and HOBT (270 mg, 1.7 mmol) respectively. The reaction mixture was stirred at room temperature for 6 hours. Sat. sodium bicarbonate aqueous solution was added to the mixture. The organic layer was extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. After the filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give the residue, which was applied to a silica gel chromatography column and eluted with a hexane/ethylacetate=2/1 (v/v) to furnish 900 mg (53% yield) of the title as a yellow solid;

后处理

  1. extractionThe organic layer was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter the filtration
  5. customto separate solvent and sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customto give the residue, which
  8. washeluted with a hexane/ethylacetate=2/1 (v/v)
  9. customto furnish 900 mg (53% yield) of the title as a yellow solid

来源与证据

ORD记录
ord-cfa6a7c8a0014b629927e1d38570f8d8
来源数据集
uspto-grants-2015_08
专利号
US09101616B2

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