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4-Toluenesulfonyl chloride → 5-chloro-N-[1-(2-chloroethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

HRID 1376156
ノート
印刷プレビュー

反応式

HRID 1376156 の反応式
C1(C)C=CC(S([Cl:10])(=O)=O)=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([C:22]([NH:24][CH:25]1[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:35][CH2:36]O)[C:26]1=[O:38])=[O:23])=[CH:16]2>N1C=CC=CC=1.C1COCC1.CCOC(C)=O>[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([C:22]([NH:24][CH:25]1[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:35][CH2:36][Cl:10])[C:26]1=[O:38])=[O:23])=[CH:16]2
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 2

HCID 73974-Toluenesulfonyl chlorideHCID 102872925-Chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

生成物 1

HCID 587884525-chloro-N-[1-(2-chloroethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide収率 47.7%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

p-Toluenesulphonyl chloride (285 mg, 1.49 mmol) was added to a solution of 5-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Example 36; 286 mg, 0.75 mmol) in pyridine (2 mL) under an inert atmosphere and stirred at ambient temperature for 18 hours. The mixture was diluted with THF (10 mL) and EtOAc (50 mL) and washed with 1M HCl aq. (20 mL), water (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:THF (9:1)) to afford the title compound (144 mg, 40%) as a yellow solid.

後処理

  1. washwashed with 1M HCl aq. (20 mL), water (20 mL), brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (DCM to DCM:THF (9:1))

出典と根拠

ORDレコード
ord-8d37bdadb25744ffbbadc8862adc4a4c
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07169927B2

反応ノート

読み込み中…

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