Sodium hydride → 11-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-7,8,9,9a,10,11-hexahydro-5H-pyrido[3',2':4,5]pyrrolo[3,2-f]indolizine

HRID 2167828노트

반응식

HRID 2167828 반응식
[CH2:1]1[CH:5]2[CH2:6][C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][N:4]2[CH2:3][CH2:2]1)=[CH:13][CH:12]=[CH:11][N:10]=4.[H-].[Na+].[O:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>CN(C=O)C>[N:25]1[CH:26]=[CH:27][C:22]([CH:20]([OH:19])[CH2:21][N:8]2[C:7]3[CH2:6][CH:5]4[N:4]([CH2:3][CH2:2][CH2:1]4)[CH2:16][C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]2=3)=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 109534834-(Oxiran-2-yl)pyridineHCID 670365602,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-cyclopenta[b]fluorene

생성물 1

HCID 5135667211-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-7,8,9,9a,10,11-hexahydro-5H-pyrido[3',2':4,5]pyrrolo[3,2-f]indolizine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-cyclopenta[b]fluorene (1 g, 4.6 mmol) in DMF (20 mL) were portion wise added NaH (60%, 0.552 g, 13.8 mmol) and 4-(oxiran-2-yl)pyridine (0.709 g, 5.6 mmol). The reaction mixture was stirred at RT overnight. The progress of reaction mass was monitored by LCMS. The reaction mixture was quenched with ice cold water (300 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with water (10×100 mL) followed by brine (2×100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography followed by reverse phase HPLC to yield the title compound.

후처리

  1. customThe progress of reaction mass
  2. customThe reaction mixture was quenched with ice cold water (300 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with water (10×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d7c4611855634c618defd12ddea57201
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045482B2

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