Hydrochloric Acid → 6-Bromo-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 1507575노트

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HRID 1507575 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.Br[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[N:8]2[CH:15]([CH3:17])[CH3:16])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 106576496-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

생성물 1

HCID 900463286-Bromo-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a suspension of 6-bromo-3,3-dimethylindolin-2-one (example 14a, 1.68 g, 7.00 mmol) in DMF (30 ml) were added 2-bromopropane (2.15 g, 1.64 ml, 17.5 mmol) and cesium carbonate (5.02 g, 15.4 mmol). The reaction mixture was heated to 80° C. for 18 hours. The reaction mixture was treated with 1 M HCl and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as orange solid (2.00 g, 70% purity) and was used for the next reaction without further purification.

후처리

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ad75f22fd8cd446d9994b117f46ea06b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221816B2

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