Cesium carbonate → HCID 71087752, Verbindung

HRID 632167

Reaktionsgleichung

Reaktionsgleichung von HRID 632167
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C1(P(C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=C(C3C4C(=CC=CC=4)C=CC=3)C3C(C=2)=CC=CC=3)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:57][O:58][C:59]([C:61]1[CH:66]=[CH:65][C:64](Br)=[C:63]([O:68][CH2:69][CH:70]2[CH2:72][CH2:71]2)[N:62]=1)=[O:60]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:57][O:58][C:59]([C:61]1[CH:66]=[CH:65][C:64]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[C:63]([O:68][CH2:69][CH:70]2[CH2:72][CH2:71]2)[N:62]=1)=[O:60]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 69828CyclopropylamineHCID 18630801Bis(diphenylphosphino)-1,1'-binaphthylHCID 71087286HCID 71087286, Verbindung

Produkt 1

HCID 71087752HCID 71087752, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Cyclopropanamine (CAS 765-30-0, 158 mg, 2.8 mmol), bis(diphenylphosphino)-1,1′-binaphthalene (CAS 98327-87-8, 115 mg, 0.19 mmol), tris(dibenzylideneacetone)dipalladium (CAS 51364-51-3, 84 mg, 0.093 mmol) and cesium carbonate (CAS 534-17-8, 1.8 g, 6.6 mmol) were added to solution of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester (Example 114 a, 530 mg, 1.85 mmol) in toluene (20 mL) under a nitrogen atmosphere. The reaction mixture was stirred overnight at 110° C. and concentrated in vacuo. The residue was dissolved in water and extracted with ethyl acetate (30 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N HCl, the resulting precipitate was collected by filtration, dried in vacuo and purified by column chromatography (silica gel, 50 g, 50% ethyl acetate in petroleum ether) to yield the title compound (400 mg, 82%) as a yellow solid; MS (EI): m/e=263.1 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate (30 mL)
  4. additionThe pH of the aqueous layer was adjusted to 2 by addition of 1 N HCl
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried in vacuo
  7. custompurified by column chromatography (silica gel, 50 g, 50% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-72cd26eb5490464d86329bead8763712
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

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