Potassium Carbonate → 6-bromo-1-(4-ethoxyphenyl)-1H-indole

HRID 1948683

反応式

HRID 1948683 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 2207001-Ethoxy-4-iodobenzeneHCID 6764936-Bromoindole

生成物 1

HCID 669202456-bromo-1-(4-ethoxyphenyl)-1H-indole収率 56.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

A solution of 1.0 g (5 mmol) of 6-bromo-1H-indole, 1.06 g (4.15 mmol) of 4-iodophenetole, 1.45 g of potassium carbonate, 38.1 mg of copper(I) iodide and 42 mg of L-proline in 15 ml of dimethyl sulfoxide is heated at 120° C. for 15 hours. The reaction mixture is then cooled to room temperature, 30 ml of water are added, and the mixture is extracted three times with 20 ml of ethyl acetate each time. After the combined organic phases have been dried over sodium sulfate, the solvent is stripped off in a rotary evaporator, and the crude product is purified by column chromatography on silica gel (n-heptane/ethyl acetate 98:2), giving 0.74 g of 6-bromo-1-(4-ethoxyphenyl)-1H-indole as brownish resin; LC/MS: 317 (M+H).

後処理

  1. extractionthe mixture is extracted three times with 20 ml of ethyl acetate each time
  2. dry with materialAfter the combined organic phases have been dried over sodium sulfate
  3. customthe solvent is stripped off in a rotary evaporator
  4. customthe crude product is purified by column chromatography on silica gel (n-heptane/ethyl acetate 98:2)

出典と根拠

ORDレコード
ord-d186617ecc044e7e8fe8929a61fdfec6
出典データセット
uspto-grants-2013_03
特許番号
US08399509B2

関連ノート

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