Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 54523

반응식

HRID 54523 반응식
[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]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 2607987-(Benzyloxy)-1H-indole

생성물 1

HCID 150540207-(Cyanomethoxy)indole

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-789f5e4231b743ab97a172bf33b31729
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622969

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