Hydrochloric Acid → HCID 57950448, Verbindung

HRID 1020666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020666
Cl.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][CH2:13][NH2:14])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Br[C:16]1[CH:24]=CC=C2[C:17]=1C(CCN)=CN2.[O-]S([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.C(O)CCC>[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]3[CH2:12][CH2:13][NH:14][C:16]([CH3:24])([CH3:17])[C:8]=3[NH:9]2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24436Sodium SulfateHCID 180714Ethanamine, 2-(6-bromo-1H-indol-3-yl)-HCID 10944501HCID 10944501, Verbindung

Produkt 1

HCID 57950448HCID 57950448, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22056974HCID 22056974, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Concentrated HCl (10 mL) was added to a suspension of a 2:1 mixture of 2-(6-bromo-1H-indol-3-yl)ethanamine and 2-(4-bromo-1H-indol-3-yl)ethanamine (9.90 g, 41.4 mmol) and Na2SO4 (30 g) in 1:1 acetone/n-butanol (100 mL). The resulting suspension was heated at 60° C. with stirring for 4 d. The suspension was cooled and concentrated under reduced pressure. The residue was diluted with EtOAc, and the suspension was filtered. The filtrate was washed with saturate NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH) 100:0 to 0:100) yielded the title compound (1.68 g, 15%) as a red foam: 1H NMR (500 MHz, CDCl3) δ 7.66 (br s, 1H), 7.45 (d, J=1.5 Hz, 1H), 7.32 (d, J=8.5 Hz, 1H), 7.19 (dd, J=8.5, 1.5 Hz, 1H), 3.20 (t, J=5.5 Hz, 2H), 2.68 (t, J=5.5 Hz, 2H), 1.47 (s, 6H).

Aufarbeitung

  1. temperatureThe suspension was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc
  4. filtrationthe suspension was filtered
  5. washThe filtrate was washed with saturate NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a463c2a6f1104ac080742ac2ff3078cd
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716308B2

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