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

HRID 1510079
ノート
印刷プレビュー

反応式

HRID 1510079 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒
HCID 6212
Chloroform
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-83d74cc4b65541d9a060479d76a0a81f
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08211885B2

反応ノート

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