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Iodoethane → 2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, ethyl ester

HRID 1492494
ノート
印刷プレビュー

反応式

HRID 1492494 の反応式
[CH2:1](I)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:10]([C:14]1[N:15]([CH2:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][N:28]3[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]#[N:40])[C:16]([C:20]([OH:22])=[O:21])=[C:17]([Cl:19])[N:18]=1)[CH2:11][CH2:12][CH3:13]>CN(C)C=O.C(OCC)(=O)C>[CH2:10]([C:14]1[N:15]([CH2:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][N:28]3[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]#[N:40])[C:16]([C:20]([O:22][CH2:1][CH3:2])=[O:21])=[C:17]([Cl:19])[N:18]=1)[CH2:11][CH2:12][CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 189503772-butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid

生成物 1

HCID 867483362-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, ethyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

Ethyl iodide (561.5 mg, 3.60 mmol) and cesium carbonate (1.5g, 4.5 mmol) were added to a solution of 2-butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5carboxylic acid (779.2 mg, 1.80 mmol, prepared as described in part C of Example 9) in dimethylformamide (3.72 ml). After 1.5 hours at room temperature, the reaction was diluted with ethyl acetate and filtered to remove the cesium carbonate. The ethyl acetate was washed with pH=4 buffer (2×20 ml), pH=7 buffer (2×25 ml), saturated sodium chloride (20 mL) and dried over anhydrous magnesium sulfate, filtered and concentrated to a yellow oil (890 mg). Purification by flash chromatography (83 g Merck silica gel, 8:2 hexane/ethyl acetate) gave 662 mg of the title A compound.

後処理

  1. filtrationfiltered
  2. customto remove the cesium carbonate
  3. washThe ethyl acetate was washed with pH=4 buffer (2×20 ml), pH=7 buffer (2×25 ml), saturated sodium chloride (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil (890 mg)
  7. customPurification by flash chromatography (83 g Merck silica gel, 8:2 hexane/ethyl acetate)
  8. customgave 662 mg of the title A compound

出典と根拠

ORDレコード
ord-8018264fad0e49f8b0dd72a53b1398a3
出典データセット
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05374615

反応ノート

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