Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 1198521

反応式

HRID 1198521 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

HCID 150540207-(Cyanomethoxy)indole

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ff6b288abf3b4fe89119d930d2236931
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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