5-Ethenylpyridine-2-carboxylic acid → 5-(2-(3,9-dimethyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl)picolinic acid

HRID 1481407Notizen

Reaktionsgleichung

[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3]1.[CH:17]([C:19]1[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=1)=[CH2:18]>[OH-].[Na+].[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:18][CH2:17][C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=3)[C:5]=2[CH2:4][CH2:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

The title compound was prepared by following general procedure 4. To a solution of 3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (200 mg, 0.93 mmol) in 50% aq. NaOH solution (3 mL) was added, tetra n-butyl ammonium chloride (12 mg, 0.046 mmol) followed by 5-vinylpicolinic acid (153 mg, 1.0 mmol). The reaction mixture was heated at 90° C. for overnight, and the reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by reverse phase chromatography to afford 7 mg of 5-(2-(3,9-dimethyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl)picolinic acid as the TFA salt.

Aufarbeitung

customThe title compound was prepared
customAfter completion of reaction
extractionextracted with ethyl acetate
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude product was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-562e37a70e7647cbb88f9b9319cd4bc8
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09409910B2

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