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Aluminium lithium hydride → N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amine

HRID 1869184
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HRID 1869184 반응식
[CH3:1][NH:2][C:3](=O)[CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydride2회HCID 68552631HCID 68552631, 화합물

생성물 1

HCID 16725756N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amine수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a RT suspension of N-methyl-3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionamide (54 mg, 0.19 mmol) in THF (5 ml) was added LiAlH4 (0.38 ml, 1M in THF) at room temperature. The resulting mixture was refluxed for 4 h, then the same amount of LiAlH4 was added. The resulting mixture was refluxed overnight, cooled to RT, quenched by addition of Na2SO4.10H2O. The mixture was stirred for 30 min and the solid was filtered off and washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) affording N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amine as a white foam (28 mg, 56% yield); MS M+H=266.

후처리

  1. temperatureThe resulting mixture was refluxed for 4 h
  2. temperatureThe resulting mixture was refluxed overnight
  3. customquenched by addition of Na2SO4.10H2O
  4. filtrationthe solid was filtered off
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated
  7. custompurified via flash chromatography (DCM/MeOH/NH4OH)

출처 및 근거

ORD 기록
ord-3db3c3e87788460abb8aeeecf7d955aa
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07638517B2

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