Benzenesulfonyl chloride → 1H-Indole-5-carboxylic acid, 1-(phenylsulfonyl)-, methyl ester

HRID 84178

Reaktionsgleichung

Reaktionsgleichung von HRID 84178
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:13][O:12][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23])[CH:2]=[CH:3]2)=[O:11]

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 2737635methyl 1H-indole-5-carboxylate

Produkt 1

HCID 575174331H-Indole-5-carboxylic acid, 1-(phenylsulfonyl)-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

After a suspension of methyl indole-5-carboxylate (1) (0.30 g, 1.71 mmol), TB AHS (0.19 g, 0.26 mmol) and KOH (0.19 g, 3.42 mmol) in CH2Cl2 (15 mL) was stirred for 20 min, benzenesulfonyl chloride (0.32 ml, 2.57 mmol) was added. The reaction mixture was stirred at room temperature overnight before it was quenched with water and 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.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature overnight before it
  2. customwas 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

Quellen und Nachweise

ORD-Eintrag
ord-109b10c8a30f45ad98f0915e1c6d9527
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846748B2

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