Sodium Carbonate → HCID 66761510, Verbindung

HRID 561834

Reaktionsgleichung

Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12](Cl)[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:34]=CC=C[CH:30]=1.[C:48](=O)([O-])[O-:49].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:11]=[C:12](/[CH:30]=[CH:29]/[CH2:34][O:49][CH3:48])[N:13]=[C:2](/[CH:19]=[CH:18]/[CH2:17][O:16][CH3:15])[CH:3]=2)[CH2:10][CH2:9]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from Amine 41, Step 1 (I eq.) in DMF (0.08 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.7 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 5 eq.). The resulting suspension was heated at 100° C. for 8 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 red oil. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-577ce0bfa216420d91f2772d3771d42c
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08063105B2

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