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Sodium Carbonate → N-Cyclopropyl-2-methoxy-6-[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

HRID 561832
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561832
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:16][O:17][CH2:18]/[CH:19]=[CH:20]/B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:3]=[C:2](/[CH:20]=[CH:19]/[CH2:18][O:17][CH3:16])[N:13]=[C:12]([O:14][CH3:15])[CH:11]=2)[CH2:10][CH2:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 845809352-Chloro-N-cyclopropyl-6-methoxyisonicotinamide

Produkt 1

HCID 66760917N-Cyclopropyl-2-methoxy-6-[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 83469Palladium bromide (PdBr2)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-chloro-N-cyclopropyl-6-methoxyisonicotinamide from the previous step (1 eq.) in DMF (0.3 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 3 eq.). The resulting suspension was heated at 100° C. for 7 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a brown tar. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) followed by recrystallization from Hex:ether afforded the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  4. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
  5. customafforded the crude product as a brown tar
  6. customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)
  7. customfollowed by recrystallization from Hex

Quellen und Nachweise

ORD-Eintrag
ord-b9f2faf003814cd486e079bdd716ec80
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063105B2

Notizen zur Reaktion

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