Methanol → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylic acid

HRID 387270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387270
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]CC)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:21][CH2:20][CH2:19][S:18](=[O:23])(=[O:22])[CH2:17]1.CO.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:21][CH2:20][CH2:19][S:18](=[O:22])(=[O:23])[CH2:17]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59332690Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

Produkt 1

HCID 593327875-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate (0.380 g, 0.949 mmol), was stirred in a methanol (5 mL)/water (3 mL) solution. 6M NaOH (1.5 mL, 0.900 mol, 10 eq) was added and the reaction was heated to 85° C. for 1.5 hours. The methanol was concentrated and the aqueous solution was acidified with 6M HCl. The resulting white solid was filtered and dried under vacuum to give 0.325 g (92%) of the title compound.

Aufarbeitung

  1. concentrationThe methanol was concentrated
  2. filtrationThe resulting white solid was filtered
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bce0ec6d60ba4a158e18d94552a33346
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372875B2

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