Potassium Carbonate → HCID 68465364, Verbindung

HRID 501176

Reaktionsgleichung

Reaktionsgleichung von HRID 501176
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[N:6][CH:5]=1.[CH2:12]1[C:17]2[NH:18][C:19]3[C:24]([C:16]=2[CH2:15][CH2:14][NH:13]1)=[CH:23][CH:22]=[CH:21][CH:20]=3.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH2:12]1[C:17]2[NH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]=2[CH2:15][CH2:14][N:13]1[C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][N:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 107838Tetrahydro-beta-carboline2×HCID 254249Methyl 6-chloropyridine-3-carboxylate

Produkt 1

HCID 68465364HCID 68465364, VerbindungAusbeute 24,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl-6-chloronicotinate (170 mg), 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (170 mg), potassium carbonate (150 mg) and dioxane (6 mL) was heated in a 100° C. oil bath overnight. Another aliquote of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (170 mg) was added and the heating was continue for five hours. The reaction was cooled and partitioned between water and EtOAc. The organics were washed with water, dried, and the solvent evaporated. The residue was purified by filtration through silica gel eluting with EtOAc to give methyl 6-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)nicotinate as a brown solid (75 mg), m/e=308 (M+1).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. custompartitioned between water and EtOAc
  3. washThe organics were washed with water
  4. customdried
  5. customthe solvent evaporated
  6. filtrationThe residue was purified by filtration through silica gel eluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e40b2c5d20dd461a9df9ecd20adfc17b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772245B2

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