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Dimethylformamide → 2-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

HRID 1510079
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HRID 1510079 반응식
CN(C=O)C.[CH2:6]([Cl:8])Cl.P(Cl)(Cl)(Cl)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:20](=[O:31])[CH2:19]2>C(Cl)(Cl)Cl.N1C=CC=CC=1.CC(=O)OCC>[Cl:8][C:6]1[N:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:22]2[C:18]([C:19]=1[CH:20]=[O:31])=[CH:17][C:16]([O:15][CH3:14])=[CH:24][CH:23]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 136034182h-Indol-2-one,1,3-dihydro-5-methoxy-1-phenyl-

생성물 1

HCID 872052842-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

시약·촉매·용매 3

HCID 1049Pyridine용매
HCID 6212
Chloroform
용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of DMF (2.3 ml) and DCM (2.3 ml) under argon was cooled to 0° C. With stirring, phosphorus oxychloride (2.14 ml, 22.9 mmol) was added within 15 min, and the mixture was stirred for further 30 min at 0° C. Then the compound of step 2 (557 mg, 2.33 mmol), dissolved in chloroform (5.77 ml) and pyridine (1.15 ml), was added to the cooled solution. The reaction mixture was stirred at room temperature overnight. The mixture was slowly poured into 300 ml of ice and after a few minutes EA was added. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography of the residue on silica gel (EA/HEP 1:8) yielded 456 mg of the title compound as a white solid.

후처리

  1. stirringthe mixture was stirred for further 30 min at 0° C
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additionwas added
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-83d74cc4b65541d9a060479d76a0a81f
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08211885B2

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