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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
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HRID 1376156 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-8d37bdadb25744ffbbadc8862adc4a4c
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169927B2

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