Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 1198521

반응식

HRID 1198521 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) was hydrogenated at 60 psi over 10% palladium on charcoal (50 mg) for 4 hours. The catalyst was 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) was 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 was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:2) to give a pale solid.

후처리

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

출처 및 근거

ORD 기록
ord-ff6b288abf3b4fe89119d930d2236931
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281593

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