Isatin → 1-(5-Chloro-thiophen-2-yl-methyl)-1h-indole-2,3-dione

HRID 218101

반응식

HRID 218101 반응식
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[Cl:14][C:15]1[S:16][C:17]([CH2:20]Cl)=[CH:18][CH:19]=1>O1CCOCC1>[Cl:14][C:15]1[S:16][C:17]([CH2:20][N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 7054IsatinHCID 24758Sodium hydrideHCID 5830792-Chloro-5-(chloromethyl)thiophene

생성물 1

HCID 220224391-(5-Chloro-thiophen-2-yl-methyl)-1h-indole-2,3-dione수율 22.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매3회

실험 절차

A solution of isatin (125 mg, 0.85 mmol) in anhydrous dioxane (10 mL) was added dropwise to a solution of sodium hydride (60% dispersion in mineral oil, 24 mg, 0.62 mmol) in anhydrous dioxane. (10 mL) at 0° C. under argon. The mixture was allowed to stir for 5 minutes and then 2-chloro-5-(chloromethyl)thiophene (0.12 mL, 1.02 mmol) in dioxane (10, mL) was added dropwise to the resulting mixture. The reaction mixture was heated at reflux under argon for 16 h and concentrated in vacuo. The crude material was purified preparative TLC using 1:24 methanol in chloroform as the eluent, giving the desired product as a yellow solid (53 mg, 0.19 mmol, 22%). 1H NMR (400 MHz): E 7.62 (d, J=7.4, 1H), 7.56 (t, J=7.8, 1H), 7.14 (t, J=7.7, 1H), 6.94 (d, J=8.0, 1H), 6.90 (d, J=3.2, 1H), 6.78 (d, J=3.7, 1H), 4.90 (s, 2H).

후처리

  1. customat 0° C.
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux under argon for 16 h
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified preparative TLC

출처 및 근거

ORD 기록
ord-75b14d7fe9f942b986eb53eb898536b3
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198313B2

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