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Cesium carbonate → (2-Boc-amino-pyridin-4-yl)-acetic acid ethyl ester

HRID 2069050
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2069050
Cl[C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1.C([NH:18][C:19](=[O:21])[O-:20])(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:28][C:29]1(C)[C:55]2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:30]1=2>C1COCC1.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]>[C:29]([O:20][C:19]([NH:18][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1)=[O:21])([CH3:55])([CH3:30])[CH3:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 21252905Tert-butylcarbamateHCID 57709236Ethyl 2-(2-chloropyridin-4-yl)acetate

Produkt 1

HCID 53419364(2-Boc-amino-pyridin-4-yl)-acetic acid ethyl esterAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of ethyl 2-(2-chloropyridin-4-yl)acetate (44) (15.0 g, 75.0 mmol), tert-butylcarbamate (26.4 g, 225 mmol), Pd2(dba)3 (1.719 g, 1.88 mmol), caesium carbonate (36.7 g, 113 mmol) and Xantphos® (2.17 g, 3.76 mmol) in THF (100 mL) was purged with nitrogen and was then stirred at 65° C. for 8 hr. The mixture was cooled to RT and was diluted with water and extracted with ether. The ether extracts were combined and washed with water and brine and then dried (MgSO4), and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 330 g, 5-20% EtOAc in isohexane, gradient elution) then subjected to SCX capture and release to provide the title compound (45) (12.0 g, 51%): m/z 281 (M+H)+ (ES+).

Aufarbeitung

  1. customwas purged with nitrogen
  2. temperatureThe mixture was cooled to RT
  3. additionwas diluted with water
  4. extractionextracted with ether
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, 330 g, 5-20% EtOAc in isohexane, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-304c5b653cc14b8fb84bee22548b805f
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299073B2

Notizen zur Reaktion

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