Water → methyl 1-(3-methoxypropyl)-3-methyl-1H-indazol-6-carboxylate

HRID 872029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872029
CB1OB(C)OB(C)O1.[C:10](=O)([O-])[O-].[K+].[K+].Br[C:17]1[C:25]2[C:20](=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=2)[N:19]([CH2:30][CH2:31][CH2:32][O:33][CH3:34])[N:18]=1.O>O1CCOCC1.Cl[Pd]Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:34][O:33][CH2:32][CH2:31][CH2:30][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:21]=2)[C:17]([CH3:10])=[N:18]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59494402methyl 3-bromo-1-(3-methoxypropyl)-1H-indazole-6-carboxylate

Produkt 1

HCID 59494412methyl 1-(3-methoxypropyl)-3-methyl-1H-indazol-6-carboxylateAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Trimethylboroxin (513 μL), potassium carbonate (1.27 g) and bis(diphenylphosphino)ferrocene dichloropalladium (224 mg) were added to a solution of methyl 3-bromo-1-(3-methoxypropyl)-1H-indazol-6-carboxylate (1.0 g) in 1,4-dioxane (15 ml) under argon atmosphere and the mixture was stirred at 110° C. for 6 hours. Water was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1 to 3/2) to give methyl 1-(3-methoxypropyl)-3-methyl-1H-indazol-6-carboxylate (705 mg) as a yellow powder.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1 to 3/2)

Quellen und Nachweise

ORD-Eintrag
ord-330e90e5ba5c43a2944f43d17faa3171
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975252B2

Notizen zur Reaktion

Wird geladen…