Potassium Carbonate → 5-Methoxy-1-phenyl-1H-indole

HRID 1510077노트

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HRID 1510077 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].I[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:7]=[CH:6]2

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 138725-MethoxyindoleHCID 145742L-Proline

생성물 1

HCID 136034295-Methoxy-1-phenyl-1H-indole수율 62.7%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

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온도
125 °C

실험 절차

To a mixture of 5-methoxyindole (1.00 g, 6.79 mmol), copper(I) iodide (129 mg, 0.68 mmol), L-proline (156 mg, 1.36 mmol) and potassium carbonate (1.88 g, 13.6 mmol) in DMSO (7.5 ml) was added iodobenzene (0.76 ml, 6.79 mmol). The reaction mixture was stirred for 10 h at 125° C. in a microwave reactor. The mixture was then quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/HEP 1:15). 951 mg of the title compound were obtained.

후처리

  1. customThe mixture was then quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (EA/HEP 1:15)

출처 및 근거

ORD 기록
ord-bbe2d10967f7493cae6f06ed057b4501
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211885B2

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