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

HRID 1507575ノート

反応式

HRID 1507575 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad75f22fd8cd446d9994b117f46ea06b
出典データセット
uspto-grants-2015_12
特許番号
US09221816B2

反応ノート

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