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Hydrochloric Acid → 2-(5-Bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

HRID 336615
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 336615
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13]C)=[O:12])[CH2:4][CH2:3][NH:2]1.Cl.[Br:16][C:17]1[C:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:19][C:20](Cl)=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[N:19][C:18]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 45074001Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylateHCID 59447676tert-Butyl 3-bromo-6-chloropyridine-2-carboxylate

Produkt 1

HCID 866812722-(5-Bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate, hydrochloric acid (13.6 g), tert-butyl 3-bromo-6-chloropicolinate (17.4 g) and cesium carbonate (39 g) were stirred together in N,N-dimethylacetamide (110 mL) and heated at 120° C. under nitrogen overnight. The reaction mixture was cooled, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and the combined aqueous layers were back-extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Silica gel chromatography using 20-100% ethyl acetate in hexanes provided the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. extractionthe combined aqueous layers were back-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f2c0a82190254ca9afbaf3c488009630
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889675B2

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