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Sodium Hydroxide → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid

HRID 656011
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 656011
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:13]([O:15]C)=[O:14])[CH:12]=1)[N:9](C(OC(C)(C)C)=O)[CH:8]=[C:7]2[CH:24]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]1.BrC1C=C2C(=C(C(OCC)=O)C=1)N(C(OC(C)(C)C)=O)C=C2C1CCS(=O)(=O)CC1>CO.O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:13]([OH:15])=[O:14])[CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:24]1[CH2:25][CH2:26][S:27](=[O:30])(=[O:31])[CH2:28][CH2:29]1
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Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 593326221-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylateHCID 593326271-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate

Produkt 1

HCID 593327515-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 6 M NaOH (12 mL, 72.0 mmol) was added to a suspension of 1-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (0.93 g, 1.912 mmol) and 1-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (3.08 g, 6.16 mmol) in MeOH (50 mL) and water (25 mL) in a 250 mL round bottomed flask fitted with a reflux condenser. The reaction was heated at 85° C. (bath temp) for 1.5 h. The MeOH was removed by rotovap, and a solution of 6 M HCl was added until the mixture had attained a pH of ˜1 by pH paper. The yellow solid was filtered off, and the filtrate was extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure, and the residue was combined with the precipitate from the filtration and dried under house vacuum at 45° C. overnight. Recovered 2.98 g (86%) of the title compound.

Aufarbeitung

  1. customfitted with a reflux condenser
  2. customThe MeOH was removed by rotovap
  3. additiona solution of 6 M HCl was added until the mixture
  4. filtrationThe yellow solid was filtered off
  5. extractionthe filtrate was extracted with EtOAc (3×10 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. filtrationthe residue was combined with the precipitate from the filtration
  9. customdried under house vacuum at 45° C. overnight
  10. customRecovered 2.98 g (86%) of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-f760ebf527f34d96bc6507df72a24984
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071584B2

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