Benzenesulfonyl chloride → 3-(1-Benzenesulfonyl-1H-indol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 84195노트

반응식

HRID 84195 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]([NH:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[O:13])=[CH:2]1.[OH-].[K+].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:24]1([S:30]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH:10]=[CH:11][C:12]([NH:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)=[O:13])=[CH:2]2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 76528170HCID 76528170, 화합물

생성물 1

HCID 866582683-(1-Benzenesulfonyl-1H-indol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide수율 54.1%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 18 (0.52 g, 1.82 mmol), tetrabutylammonium bisulfate (0.09 g, 0.27 mmol) and KOH (0.20 g, 3.63 mmol) in CH2Cl2 (15 mL) was stirred for 20 min, benzenesulfonyl chloride (0.35 ml, 2.72 mmol) was added and stirred at room temperature overnight. The reaction mixture was quenched with water extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 19 (0.42 g)

후처리

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with CH2Cl2 (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:2)

출처 및 근거

ORD 기록
ord-88f6205fddcf492db24f869888c02aac
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846748B2

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