Methyl vinyl ketone → 2-(2-(Imidazo[1,2-a]pyridin-2-yl)ethyl)isoindoline-1,3-dione

HRID 1790047노트

반응식

HRID 1790047 반응식
C=CC(=O)C.C1(=O)NC(=O)C2=CC=CC=C12.[Br:17][CH2:18][C:19](=[O:33])[CH2:20][CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1>C(O)C>[Br:17][CH2:18][C:19](=[O:33])[CH2:20][CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].[N:34]1[C:19]([CH2:20][CH2:21][N:22]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])=[CH:18][N:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=12

참가 물질

7

반응물 4

HCID 6570Methyl vinyl ketoneHCID 6809PhthalimideHCID 104392-AminopyridineHCID 37597442-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dione

생성물 2

HCID 15312692-(2-(Imidazo[1,2-a]pyridin-2-yl)ethyl)isoindoline-1,3-dione수율 96.6%HCID 37597442-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-(4-Bromo-3-oxo-butyl)-isoindole-1,3-dione is prepared by condensation of but-1-en-3-one with phthalimide followed by bromination according to known procedures (J. Med. Chem., 35:3239, 1992. A solution of 2-(4-bromo-3-oxo-butyl)-isoindole-1,3-dione (8.9 g, 30.06 mmol) and 2-aminopyridine (2.8 g, 29.75 mmol) in ethanol is heated at reflux for 4 hours. The mixture is cooled to room temperature and concentrated. The residue is purified by chromatography (silica gel, dichloromethane/ethanol 95:5); to give 4.23 g of 2-[2-(imidazo[1,2-a]pyridin-2-yl)ethyl]-isoindole-1,3-dione (49%).

후처리

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated
  3. customThe residue is purified by chromatography (silica gel, dichloromethane/ethanol 95:5)

출처 및 근거

ORD 기록
ord-03251ddc1f3e4d94aef166f6ac65dfbe
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071208B2

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