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Hydrochloric Acid → 4-Tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazole

HRID 1604658
ノート
印刷プレビュー

反応式

HRID 1604658 の反応式
[H-].[Na+].[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)#[N:4].[C:15]([C:19]1[N:20]=[C:21]([C:24]2[O:25][C:26]3[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][C:27]=3[CH:28]=2)[S:22][CH:23]=1)([CH3:18])([CH3:17])[CH3:16].[I-].[K+].Cl>CN(C)C=O>[C:15]([C:19]1[N:20]=[C:21]([C:24]2[O:25][C:26]3[CH:32]=[CH:31][C:30]([CH2:33][N:7]4[C:8]5[C:13](=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=5)[C:5]([C:3]#[N:4])=[CH:6]4)=[CH:29][C:27]=3[CH:28]=2)[S:22][CH:23]=1)([CH3:18])([CH3:17])[CH3:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 19603727HCID 19603727、化合物HCID 196038046-Methyl-1H-indole-3-carbonitrile

生成物 1

HCID 196038354-Tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazole収率 100.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in mineral oil, 30 mg) was added into a solution of 3-cyano-6-methylindole (73 mg) in N,N-dimethylformamide (2 ml) at room temperature. After 30 minutes, 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (150 mg) and small amount of potassium iodide were added to the solution. After being stirred continuously for 3 hours, the resulting mixture was poured into ice-water and the mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazole (0.2 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of toluene and ethyl acetate
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fd2af3e2cad249369c26969eeb886719
出典データセット
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05994378

反応ノート

読み込み中…

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