Potassium Carbonate → HCID 86681614, 화합물

HRID 571195

반응식

HRID 571195 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC#N>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:10]=[CH:9]2)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 233967-NitroindoleHCID 60984Methyl bromoacetate2회

생성물 1

HCID 86681614HCID 86681614, 화합물수율 51%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 7-nitro-1H-indole (0.5 g, 3.08 mmol) in dry CH3CN (20 ml), K2CO3 (0.511 g, 3.70 mmol) was added at room temperature. After 10 minutes, methyl 2-bromoacetate (0.343 ml, 3.70 mmol) was added dropwise, and the reaction was refluxed for 24 hours. Additional K2CO3 (0.511 g, 3.70 mmol) and methyl 2-bromoacetate (0.343 ml, 3.70 mmol) were added, and the stirring was prolonged for further 16 hours. The reaction was cooled at room temperature and the solvent was evaporated under vacuum. The resulting crude was partitioned between water and DCM; the organic phase was dried over sodium sulfate and evaporated under vacuum. The crude was purified by flash column chromatography on silica gel (hexane:ethyl acetate=9:1) affording methyl 2-(7-nitro-1H-indol-1-yl)acetate that crystallizes on standing (0.37 g, 1.580 mmol, 51% yield). MS/ESI+ 234.9 [MH]+.

후처리

  1. temperaturethe reaction was refluxed for 24 hours
  2. waitthe stirring was prolonged for further 16 hours
  3. customthe solvent was evaporated under vacuum
  4. customThe resulting crude was partitioned between water and DCM
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe crude was purified by flash column chromatography on silica gel (hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-3b88eb2600b1460fb4224f3d9fb5ecd4
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024027B2

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