Hydrochloric Acid → 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylic acid

HRID 42502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42502
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+].Cl>CO.O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 67466539methyl 6-bromo-1-isopropyl-1H-indole-4-carboxylate

Produkt 1

HCID 674686386-bromo-1-(1-methylethyl)-1H-indole-4-carboxylic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylate (0.52 g, 1.756 mmol) in methanol (15 mL) and tetrahydrofuran (3 mL) was added 3 M NaOH (1.756 mL, 5.27 mmol) via syringe drop wise (over 2 min). The solution was maintained at RT for 2 h, at which time LCMS showed only 12% conversion to product. Then 1.5 mL 3 M NaOH was added and the solution was maintained at RT overnight. LCMS showed complete conversion to product. Removed volatiles in vacuo and dissolved the residue in water and slowly acidified with 1 M HCl (solids precipitated). Extracted with EtOAc (2×), combined organics and dried over MgSO4. Filtered and concentrated in vacuo to give 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylic acid (0.50 g, 1.737 mmol, 99% yield) as a white solid.

Aufarbeitung

  1. temperaturethe solution was maintained at RT overnight
  2. extractionExtracted with EtOAc (2×)
  3. dry with materialdried over MgSO4
  4. filtrationFiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9f397c2dfa8c47269edee169440dd3fa
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536179B2

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