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1,2-Dimethoxyethane → Methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoate

HRID 596080
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596080
CC1(C)C(C)(C)OB([C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)O1.Br[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:28])[CH:19]=1.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.CCCCCCC.CCOCC>[NH2:15][C:10]1[C:9]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:28])[CH:19]=2)=[CH:14][CH:13]=[CH:12][N:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 22031226Methyl 4-bromo-2-methylbenzoateHCID 438110672-Aminopyridine-3-boronic acid, pinacol ester

Produkt 1

HCID 118046459Methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoateAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807
HCID 178418807, Verbindung
Katalysator
HCID 3283Diethyl EtherLösungsmittel
HCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
108 °C

Versuchsvorschrift

To 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine(7.37 g, 33.5 mmol) in 500 mL round bottom flask were added methyl 4-bromo-2-methylbenzoate (6.390 g, 27.9 mmol), PdCl2(dppf)-DCM (2.041 g, 2.79 mmol), DME (209 mL) and 2 M Na2CO3 solution (69.7 mL). The reaction mixture was bubbled through N2 for 20 min and heated in an oil bath at 108° C. for 1.5 h. The reaction mixture was diluted with EtOAc, washed with water three times, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography eluting with 0-100% of EtOAc (containing 10% of MeOH)/heptane to provide crude product around 8 g which contained fair amount of B2(PIN)2 from previous experiment. Ether was added to dissolve the crude mixture, and then heptane was added to crush out the desired product. Solid was filtered out to provide 4.2 g of desired product with high purity in 62.1% yield. LCMS (m/z): 243.5 (MH+), 0.56 min.

Aufarbeitung

  1. customThe reaction mixture was bubbled through N2 for 20 min
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with water three times
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 0-100% of EtOAc (containing 10% of MeOH)/heptane
  9. customto provide crude product around 8 g which

Quellen und Nachweise

ORD-Eintrag
ord-e08fcfd5f86c4dfaa9ca0ddc469a300a
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242996B2

Notizen zur Reaktion

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