Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 1198562

반응식

HRID 1198562 반응식
Cl[C:2]1[CH:11]=[C:10]2[C:5](C=C[C:8](/[CH:12]=C/C3C=C(C=CC=3)CO)=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:23][C:24]#[N:25].C(=O)([O-])[O-:27].[K+].[K+]>CO.C1(C)C=CC=CC=1.[OH-].[OH-].[Pd+2]>[C:24]([CH2:23][O:27][C:5]1[CH:4]=[CH:3][CH:2]=[C:11]2[C:10]=1[NH:9][CH:8]=[CH:12]2)#[N:25]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 10827738trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl alcohol

생성물 1

HCID 150540207-(Cyanomethoxy)indole

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

The protected 7-substituted indole (Example 34a part ii) (0.53 g, 1.75 mmol) in methanol (10 ml) and toluene (10 ml) was hydrogenated in a Parr apparatus at 50 p.s.i. for 1 hour in the presence of Pearlman's catalyst (0.33 g). The reaction mixture was filtered through Celite and the filtrate evaporated in vacuo. The crude 7-hydroxy indole was taken up in methyl ethyl ketone (20 ml), and bromoacetonitrile (0.65 g, 5.25 mmol) and anhydrous potassium carbonate (0.6 g, 4.35 mmol) added. The mixture was refluxed under nitrogen for 1 hour, cooled, poured into 2.5M hydrochloric acid/ice and extracted into dichloromethane. The organic phase was washed with water, dried, filtered and evaporated in vacuo.

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate evaporated in vacuo
  3. temperatureThe mixture was refluxed under nitrogen for 1 hour
  4. temperaturecooled
  5. extractionextracted into dichloromethane
  6. washThe organic phase was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-cfb28e7ed3b24622adf9dc9b1f6170ad
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281593

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