1-Bromo-3-chloropropane → 5-(3-Chloro-propoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 132816

Reaktionsgleichung

Reaktionsgleichung von HRID 132816
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:17][CH2:18][CH2:19][Cl:20])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Produkt 1

HCID 451123565-(3-Chloro-propoxy)-1H-indole-2-carboxylic acid ethyl esterAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of ethyl-5-hydroxyindole-2-carboxylate (purchased at Biosynth, Ref H-6350, 15 g, 1.0 eq.), 1-bromo-3-chloropropane (8.8 mL, 1.2 eq.) and potassium carbonate (12.12 g, 1.2 eq.) in butanone (200 mL) was stirred 4 days at reflux. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, evaporated in vacuo and purified on silica, eluting with a 19:1 to 2:1 gradient of cyclohexane/ethyl acetate to yield 15.3 g (74%) of the desired product as light yellow solid. MS (m/e): 282.5 (MH+, 100%).

Aufarbeitung

  1. temperatureat reflux
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. customevaporated in vacuo
  6. custompurified on silica
  7. washeluting with a 19:1 to 2:1 gradient of cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f255e45802724c42866eefe1e752fc19
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388095B2

Verknüpfte Notizen

Wird geladen…