Cesium carbonate → Methyl 7-(2,2-dimethyl-propionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate

HRID 715968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715968
Br[C:2]1[C:3]([CH2:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][NH:22]2)=[C:4]([C:9]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:14]([CH3:17])([CH3:16])[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:2]2[N:22]3[CH2:23][CH2:24][CH2:25][CH:21]3[CH2:20][CH2:19][C:3]=2[C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:18]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 70982675Methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoate2×

Produkt 1

HCID 70983965Methyl 7-(2,2-dimethyl-propionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylateAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)-benzoate (Intermediate 35, 2.05 g), palladium acetate (0.282 g), cesium carbonate (3.26 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (1.557 g) in toluene (40 mL) was stirred and heated at 100° C. under nitrogen for one hour. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30% to give methyl 7-(2,2-dimethylpropionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate (0.826 g) as a pale yellow solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%

Quellen und Nachweise

ORD-Eintrag
ord-e64dfdef5a6f460385b3dba91bb4f549
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187494B2

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