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Benzenesulfonyl chloride → Methyl 1-(Phenylsulfonyl)indoline-5-carboxylate

HRID 84186
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HRID 84186 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH2:9][CH2:8]2)=[O:4].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])=[O:21])[CH2:9][CH2:8]2)=[O:4]
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참가 물질

4

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylate

생성물 1

HCID 31756086Methyl 1-(Phenylsulfonyl)indoline-5-carboxylate수율 79.8%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 10 (0.28 g, 1.58 mmol) in pyridine (2 mL), benzenesulfonyl chloride (0.40 ml, 3.16 mmol) was added. The reaction mixture was refluxed overnight. The mixture was then purified by silica gel chromatography (EtOAc:n-hexane=1:3) to afford 11 (0.40 g). 1H NMR (500 MHz, CDCl3): δ 2.99 (t, J=8.6 Hz, 2H), 3.87 (s, 3H), 3.97 (t, J=8.6 Hz, 2H), 7.45-7.48 (m, 2H), 7.56-7.59 (m, 1H), 7.66 (d, J=8.5 Hz, 1H), 7.75 (s, 1H), 7.82 (d, J=7.7 Hz, 2H), 7.90 (d, J=7.9 Hz, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe mixture was then purified by silica gel chromatography (EtOAc:n-hexane=1:3)

출처 및 근거

ORD 기록
ord-e17eed0756ca4c2090bb49cc71ff4a39
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846748B2

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