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

HRID 1510077ノート

反応式

HRID 1510077 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 136034295-Methoxy-1-phenyl-1H-indole収率 62.7%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bbe2d10967f7493cae6f06ed057b4501
出典データセット
uspto-grants-2012_07
特許番号
US08211885B2

反応ノート

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