Sodium Hydroxide → 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylic acid

HRID 516768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516768
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([O:18]C)=[O:17])[C:5]2[C:6]([CH3:15])=[CH:7][N:8]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+].CC(OC)(C)C>CO.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=[O:17])[C:5]2[C:6]([CH3:15])=[CH:7][N:8]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:9]=2[CH:10]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 67465536Methyl 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylate

Produkt 1

HCID 674653226-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylate (3.24 g, 9.99 mmol) was dissolved in methanol (30 mL) and tetrahydrofuran (THF) (7 mL). The contents were stirred for 5 min., and then aq. 3N NaOH (19.99 mL, 60.0 mmol) was added via addition funnel over 3 min. The contents rapidly became a yellow suspension and were stirred at room temperature for 65 h. The volatiles were removed in vacuo and the residue dissolved in water (60 mL). The contents were washed with ether (1×50 mL). The aq layer was cooled in an ice bath and adjusted to pH 3-4 with 1M HCl, from which an oily residue precipitated. The contents were extracted with EtOAc (2×60 mL). The combined organic layers were dried over magnesium sulfate, filtered through celite, and concentrated in vacuo. The residue obtained was treated with TBME, concentrated in vacuo, and then dried under hi vacuum to afford a yellow foam as 3.08 g (93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70 (t, J=7.33 Hz, 3H), 1.39 (d, J=6.82 Hz, 3H), 1.71-1.86 (m, 2H), 2.30 (s, 3H), 4.48-4.62 (m, 1H), 7.40-7.49 (m, 2H), 7.96 (d, J=1.77 Hz, 1H), 12.99 (s, 1H); LCMS=310.0/312.0 (MH+).

Aufarbeitung

  1. stirringwere stirred at room temperature for 65 h
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe residue dissolved in water (60 mL)
  4. washThe contents were washed with ether (1×50 mL)
  5. temperatureThe aq layer was cooled in an ice bath
  6. customprecipitated
  7. extractionThe contents were extracted with EtOAc (2×60 mL)
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered through celite
  10. concentrationconcentrated in vacuo
  11. customThe residue obtained
  12. concentrationconcentrated in vacuo
  13. customdried under hi vacuum
  14. customto afford a yellow foam as 3.08 g (93%)

Quellen und Nachweise

ORD-Eintrag
ord-280098a5c17e44c0a0e9ecc2de1de5f7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09114141B2

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