Sodium Carbonate → 3-Nitro-5-phenylpicolinonitrile

HRID 69938

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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>[N+:10]([C:4]1[C:5]([C:8]#[N:9])=[N:6][CH:7]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1)([O-:12])=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

5-bromo-3-nitropicolinonitrile (1 eq) and phenylboronic acid (1.5 eq) was mixed with 15 mL of 1,4-dioxane and 5 mL of 2 M Na2CO3 aqueous solution in a glass pressure tube. The reaction mixture was degassed by anhydrous N2 stream for 5 min followed by the addition of Pd(dppf)Cl2-DCM (0.1 eq). The reaction mixture was stirred at 100° C. for 3 hours. Then the mixture was diluted with 100 mL of ethyl acetate and washed with water, brine, then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was triturated by DCM, ether, hexanes to give the pure titled compound. LC/MS (m/z): 226.1 (MH+).

Aufarbeitung

customThe reaction mixture was degassed by anhydrous N2 stream for 5 min
washwashed with water, brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under reduced pressure
customto give crude product, which
customwas triturated by DCM, ether, hexanes

Quellen und Nachweise

ORD-Eintrag: ord-d9bd29a468344207916a81149c67d060
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822497B2

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