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Sodium hydride → 1-(4-Allyl-2,4,8-trimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-yl-propan-2-ol

HRID 576531
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HRID 576531 반응식
[CH2:1]([C:4]1([CH3:19])[C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7][N:6]([CH3:18])[CH2:5]1)[CH:2]=[CH2:3].[H-].[Na+].[CH3:22][C:23]1([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:25][O:24]1>CN(C=O)C>[CH2:1]([C:4]1([CH3:19])[C:9]2[N:10]([CH2:22][C:23]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)([OH:24])[CH3:25])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7][N:6]([CH3:18])[CH2:5]1)[CH:2]=[CH2:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 123953864-(2-Methyloxiran-2-yl)pyridineHCID 673559434-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

생성물 1

HCID 673556601-(4-Allyl-2,4,8-trimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-yl-propan-2-ol수율 46.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매
2회

실험 절차

4-Allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1 g, 3.9 mmol) was dissolved in DMF (10 mL) and stirred for 10 min at RT. Sodium hydride (475 mg, 11.7 mmol) was added portionwise and stirring was continued for 15 min at RT. 4-(2-Methyl-oxiranyl)-pyridine (690 mg, 5.1 mmol) diluted in DMF was added dropwise at RT and the reaction mixture was further stirred for 16 h after which it was quenched with ice water and extracted with EtOAc (3×70 mL). The combined organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized in ether to obtain 700 mg of 1-(4-Allyl-2,4,8-trimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-yl-propan-2-ol.

후처리

  1. stirringstirring
  2. waitwas continued for 15 min at RT
  3. additionwas added dropwise at RT
  4. stirringthe reaction mixture was further stirred for 16 h after which it
  5. customwas quenched with ice water
  6. extractionextracted with EtOAc (3×70 mL)
  7. washThe combined organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized in ether

출처 및 근거

ORD 기록
ord-ea42c95346ae42ce8dc376d1078dfd85
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040519B2

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