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

HRID 1492491
ノート
印刷プレビュー

反応式

HRID 1492491 の反応式
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([OH:13])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46]>>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([O:13][CH:49]([O:48][C:45](=[O:47])[CH3:46])[CH3:50])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]
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 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 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 57250442
2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 1-(acetyloxy)ethyl ester

実験手順

2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid (910 mg, 2.1 mmol, prepared as described in part C of Example 9), the title B compound (930 mg, 7.6 mmol), sodium iodide (795 mg, 5.03 mmol), cesium carbonate (2.6 g, 7.98 mmol) and dimethylformamide (4.0 mL) were combined and were stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate and filtered. The organic phase was washed with pH=4 buffer twice, pH 7 buffer once, saturated sodium chloride once, dried over anhydrous magnesium sulfate, filtered and concentrated to give a yellow oil. Purification by chromatography on Merck silica gel (250 g) eluting with (8:2) hexane/ethyl acetate gave the title B compound (1.06 g).

後処理

  1. filtrationfiltered
  2. washThe organic phase was washed with pH=4 buffer twice
  3. dry with materialpH 7 buffer once, saturated sodium chloride once, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by chromatography on Merck silica gel (250 g)
  8. washeluting with (8:2) hexane/ethyl acetate

出典と根拠

ORDレコード
ord-a345282878464c6a8a32c4d9636a29c7
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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