Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 1198562

反応式

HRID 1198562 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 150540207-(Cyanomethoxy)indole

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cfb28e7ed3b24622adf9dc9b1f6170ad
出典データセット
uspto-grants-1994_01
特許番号
US05281593

関連ノート

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