Sodium hydride → HCID 67320104, 화합물

HRID 1619479노트

반응식

HRID 1619479 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 67320104HCID 67320104, 화합물수율 111.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eac464fbaa3841eaa737ab0ee1ebe37e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772311B2

반응 노트

불러오는 중…