Cesium carbonate → 5-(3-Dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

HRID 1820556노트

반응식

HRID 1820556 반응식
[CH3:1][N:2]([CH3:25])[CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]3)=[O:10])[CH2:4]1.[CH:26](CS([O-])(=O)=O)([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:23]([O:22][C:20]([C:15]1[N:16]([CH:26]([CH3:28])[CH3:27])[C:17]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:9]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([N:2]([CH3:25])[CH3:1])[CH2:4]1)=[O:10])=[CH:19][CH:18]=2)=[O:21])[CH3:24]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 22141912Isopropyl-methanesulfonateHCID 68680571Ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

생성물 1

HCID 686800365-(3-Dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate (1.51 g, 4 mmol) in acetonitrile (30 ml) were added isopropylmethane-sulfonate (1.8 eq, 1.1 g) and caesium carbonate (1.8 eq, 2.6 g). The mixture was heated overnight at reflux. The solvent was evaporated under reduced pressure and the residue partitioned between water and tert-butylmethyl ether. The phases were separated, the aqueous phase extracted with tert-butylmethyl ether and the combined organic phases washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant) to afford the product as a light-brown gum. (31%)

후처리

  1. temperatureThe mixture was heated overnight
  2. temperatureat reflux
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and tert-butylmethyl ether
  5. customThe phases were separated
  6. extractionthe aqueous phase extracted with tert-butylmethyl ether
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant)

출처 및 근거

ORD 기록
ord-86084123834040b5bc2ad0546aad22f5
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601711B2

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