Ethyl 2-aminobenzoate → Ethyl acetate hexane

HRID 42070

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:6][CH:7]=1.[NH2:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:8].[C:19]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:18].[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH:16][C:17]3[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=3[C:19]([OH:21])=[O:20])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.

Aufarbeitung

customThe solvent was evaporated
customthe solid residue was triturated with aqueous solution of 2N HCl
extractionextracted with CHCl3

Quellen und Nachweise

ORD-Eintrag: ord-0c6010783c884be28f919b4217d37301
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536165B2

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