Sodium Hydroxide → 6-bromo-1-cyclopropyl-1H-indole-4-carboxylic acid

HRID 516770

Reaktionsgleichung

Reaktionsgleichung von HRID 516770
[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]3[CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[OH-].[Na+]>CO.C1COCC1>[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]3[CH2:13][CH2:12]3)[C:9]=2[CH:10]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67467490methyl 6-bromo-1-cyclopropyl-1H-indole-4-carboxylate

Produkt 1

HCID 674651346-bromo-1-cyclopropyl-1H-indole-4-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 6-bromo-1-cyclopropyl-1H-indole-4-carboxylate (0.43 g, 1.462 mmol) in MeOH (12 mL) and THF (3 mL) was added 3 M NaOH (1.949 mL, 5.85 mmol). The reaction was stirred for 18 h at RT, at which time the volatiles were removed in vacuo. The residue was diluted with water and slowly acidified with 1 N HCl to pH 4-5, then extracted with EtOAc (2x). The combine organics were wash with brine, dried over magnesium sulfate, filtered, and concentrated to give 6-bromo-1-cyclopropyl-1H-indole-4-carboxylic acid (0.376 g, 1.315 mmol, 90% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.01 (m, 2H) 1.05-1.12 (m, 2H) 3.51 (tt, J=7.07, 3.66 Hz, 1H) 6.89 (d, J=2.53 Hz, 1H) 7.52 (d, J=3.03 Hz, 1H) 7.80 (d, J=1.77 Hz, 1H) 7.99 (d, J=1.01 Hz, 1H) 13.05 (br. s., 1H). MS(ES) [M+H]+ 280.1.

Aufarbeitung

  1. customwere removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (2x)
  4. washThe combine organics were wash with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cba2e33165e04484942ef52fa85755ec
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09114141B2

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