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

HRID 859124노트

반응식

HRID 859124 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.[Br:14][C:15]1[C:16]([NH:18][C:19](=[O:22])[C:20]=1[Br:21])=[O:17].[Cl-].[NH4+]>C1(C)C=CC=CC=1.ClCCl.O1CCCC1>[CH2:3]([Mg:1][Br:14])[CH3:4].[Br:21][C:20]1[C:19](=[O:22])[NH:18][C:16](=[O:17])[C:15]=1[C:7]1[C:8]2[C:13](=[N:12][CH:11]=[CH:10][CH:9]=2)[NH:5][CH:6]=1

참가 물질

10

반응물 5

HCID 6332Ethyl BromideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14279DibromomaleimideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 2

HCID 695953123-bromo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dioneHCID 178418443HCID 178418443, 화합물

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  1. additionis added dropwise
  2. stirringAfter 1 hour 30 minutes' stirring at ambient temperature
  3. waitAfter 20 minutes
  4. extractionThe organic product is extracted with ethyl acetate
  5. dry with materialthe combined organic phases are dried over magnesium sulphate
  6. filtrationfiltered
  7. customAfter removal of the solvent
  8. customby evaporation, and purification of the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2)

출처 및 근거

ORD 기록
ord-20edb44dbc39443e9703e9400d7659fb
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151108B2

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