Tetrahydrofuran → 5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid

HRID 1042109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042109
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([O:30]CC)=[O:29])=[CH:15]3)=[N:9][CH:10]=1)(=[O:4])=[O:3].[OH-].[Na+].O1CCCC1>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:20]=2)[NH:17][C:16]([C:28]([OH:30])=[O:29])=[CH:15]3)=[N:9][CH:10]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66726001HCID 66726001, Verbindung

Produkt 1

HCID 667259135-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acidAusbeute 109,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of ethyl 5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylate (4.0 g), 1M aqueous sodium hydroxide solution (13 mL), tetrahydrofuran (20 mL), and ethanol (20 mL) was stirred at 50° C. for 50 min. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in water. 1M Hydrochloric acid (13.2 mL) was added and the precipitated yellow solid was collected by filtration. The obtained solid was washed with water and diethyl ether to give the title compound (4.1 g, yield 100%) as a yellow solid.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. addition1M Hydrochloric acid (13.2 mL) was added
  4. filtrationthe precipitated yellow solid was collected by filtration
  5. washThe obtained solid was washed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-cf051521010c4ff18e497f4969966155
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557805B2

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