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Ethyl Bromide → 3-Bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione

HRID 891000
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HRID 891000 반응식
[Mg:1].Br[CH2:3][CH3:4].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][N:12]=2)[CH:7]=[CH:6]1.[CH3:14][N:15]1[C:19](=[O:20])[C:18]([Br:21])=[C:17]([Br:22])[C:16]1=[O:23].[Cl-].[NH4+]>C1(C)C=CC=CC=1.ClCCl.O1CCCC1>[CH2:3]([Mg:1][Br:21])[CH3:4].[Br:22][C:17]1[C:16](=[O:23])[N:15]([CH3:14])[C:19](=[O:20])[C:18]=1[C:7]1[C:8]2[C:13](=[N:12][CH:11]=[CH:10][CH:9]=2)[NH:5][CH:6]=1
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참가 물질

10

반응물 5

HCID 6332Ethyl BromideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 181552,3-Dibromo-N-methylmaleimideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 2

HCID 130062143-Bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione
HCID 178418443
HCID 178418443, 화합물

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethylmagnesium bromide is prepared, starting from magnesium (12.7 mmol) suspended in bromoethane (12.7 mmol) and dry tetrahydrofuran (5 ml). The solution is stirred at ambient temperature for 1 hour and then 7-azaindole (12.7 mmol), dissolved in 40 ml of anhydrous toluene, is added dropwise. After stirring at ambient temperature for 1 hour 30 minutes, a solution of N-methyl-2,3-dibromomaleimide (3.53 mmol) in 40 ml of anhydrous toluene is added dropwise. After 20 minutes, 60 ml of dry dichloromethane are added; the reaction mixture is then stirred at 40° C. for 75 hours and hydrolysed with saturated aqueous ammonium chloride solution. The organic product is extracted with ethyl acetate, and the organic phases are then combined, dried over magnesium sulphate and filtered. After evaporating off the solvent and purifying the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2), the expected product is isolated.

후처리

  1. additionis added dropwise
  2. stirringAfter stirring at ambient temperature for 1 hour 30 minutes
  3. waitAfter 20 minutes
  4. extractionThe organic product is extracted with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customAfter evaporating off the solvent
  8. custompurifying the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2)

출처 및 근거

ORD 기록
ord-f2c7b550815040e98b849e8a6a3f822c
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07001906B2

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