Sodium hydride → HCID 67320104、化合物

HRID 1619479ノート

反応式

HRID 1619479 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:2]=1.[H-].[Na+]>CN(C=O)C>[C:6]1([CH2:5][CH2:4][CH2:3][N:12]2[C:13]3[CH:1]=[N:2][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

生成物 1

HCID 67320104HCID 67320104、化合物収率 111.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Compound 10 (1.2 g, 5 mmol) was mixed with DMF (30 ml). After stirring the mixture at room temperature for 15 minutes, NaH (0.6 g, 15 mmol) was added and stirred until the solution became clear. After that, 1-bromine-3-phenylpropane (2 ml) was added. The mixture was refluxed for 4 h. THF was evaporated in reduced pressure. The resulting solution was added 200 ml 2N HCl solution. The mixture was extracted with ethyl ether. The aqueous phase was neutralized by saturated NaHCO3 solution and then extracted with ethyl acetate. The organic phases were combined, washed with water and brine, dried over sodium sulfate, filtered, concentrated in vacuum and purified with silica gel column chromatography with ethyl acetate as the eluent. Upon recrystallization, white needle crystals (1.0 g, 56%) were obtained, mp 140-142° C.

後処理

  1. stirringstirred until the solution
  2. temperatureThe mixture was refluxed for 4 h
  3. customTHF was evaporated in reduced pressure
  4. additionThe resulting solution was added 200 ml 2N HCl solution
  5. extractionThe mixture was extracted with ethyl ether
  6. extractionextracted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuum
  11. custompurified with silica gel column chromatography with ethyl acetate as the eluent
  12. customUpon recrystallization

出典と根拠

ORDレコード
ord-eac464fbaa3841eaa737ab0ee1ebe37e
出典データセット
uspto-grants-2014_07
特許番号
US08772311B2

反応ノート

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