1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-Bromo-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester

HRID 1355657노트

반응식

HRID 1355657 반응식
[C:1]([O:5][C:6](=[O:23])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[NH2:22])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl.N12CCCN=C1CCCCC2>ClCCl>[C:1]([O:5][C:6]([C:7]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:15]2[C:16](=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[NH:22][C:34]1=[O:36])=[O:23])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 700318672-(2-Amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester

생성물 1

HCID 700343386-Bromo-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester수율 130.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-(2-Amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester (10.00 g, 25.9 mmol) and diisopropylethyl amine (22.6 ml, 129.6 mmol) were dissolved in 100 ml of anhydrous dichloromethane (DCM) under an atmosphere of dry N2. The solution was cooled to 0° C. and triphosgene (2.82 g, 9.50 mmol) was added portionwise over a period of 15 minutes. After the addition was complete, the reaction mixture was warmed to ambient temperature and stirred for 1.5 hours after which time 1,8-diazabicyclo[5.4.0]undec-7-ene (19.4 ml, 129.5 mmol) was added and the mixture was stirred for an additional 1 hour. The reaction mixture was then partitioned between water and DCM. The DCM layer was then washed 3 times with 10% aqueous NaHSO4, dried over MgSO4, filtered and concentrated under vacuum to give a green foam. The green foam was stirred in hexanes overnight. The precipitate was collected and washed with hexanes, dried under vacuum to give 5.10 g of the titled compound as a white solid.

후처리

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warmed to ambient temperature
  3. additionwas added
  4. customThe reaction mixture was then partitioned between water and DCM
  5. washThe DCM layer was then washed 3 times with 10% aqueous NaHSO4
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a green foam
  10. customThe precipitate was collected
  11. washwashed with hexanes
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-1ab2754d3765466682a2d404ae0d51a9
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586447B1

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