碳酸钾 → 7-(氰基甲氧基)吲哚

HRID 866028

反应方程式

HRID 866028 反应方程式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1C=CC=CC=1.BrCC#[N:21].C(=O)([O-])[O-].[K+].[K+]>CO.[Pd].C(C(C)=O)C>[C:2]([CH2:1][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)#[N:21]

参与物

7

反应物 3

HCID 11430碳酸钾HCID 11534溴乙腈HCID 2607987-苄氧基吲哚

产物 1

HCID 150540207-(氰基甲氧基)吲哚

试剂、催化剂与溶剂 3

HCID 23938钯催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 65692-丁酮溶剂

实验过程

A solution of 7-benzyloxyindole (0.5 g, 2.24 mmol) in methanol (100 ml) is hydrogenated at 60 psi (4.38 Kg/cm2) over 10% palladium on charcoal (50 mg) for 4 hours. The catalyst is filtered off and the filtrate was evaporated. A stirred solution of the residue and bromoacetonitrile (0.16 ml, 2.3 mmol) in methyl ethyl ketone (5 ml) is heated under reflux with solid anhydrous potassium carbonate (0.62 g, 4.5 mmol) for 2 hours, cooled, poured onto ice-hydrochloric acid and extracted with dichloromethane. The extract is dried and evaporated and the residue is chromatographed on silica in ethyl acetate-hexane (1:2) to give a pale solid.

后处理

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate was evaporated
  3. temperaturecooled
  4. additionpoured onto ice-hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customThe extract is dried
  7. customevaporated
  8. customthe residue is chromatographed on silica in ethyl acetate-hexane (1:2)
  9. customto give a pale solid

来源与证据

ORD记录
ord-7c6abb8e5c054b43beb7d6a75eb9fc19
来源数据集
uspto-grants-1996_10
专利号
US05569764

关联笔记

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