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

HRID 84195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84195
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 866582683-(1-Benzenesulfonyl-1H-indol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamideAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-88f6205fddcf492db24f869888c02aac
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846748B2

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