Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 375682

反応式

HRID 375682 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) 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.

後処理

  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

出典と根拠

ORDレコード
ord-4c6aae2296174cc790b579f85ad74fbc
出典データセット
uspto-grants-1996_01
特許番号
US05486612

関連ノート

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