4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester → 4-[3-Oxo-3-(2-phenylamino-pyridin-3-yl)-propyl]-benzoic acid methyl ester

HRID 1261761

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](=[O:26])[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:5]=1.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12](=[O:26])[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A mixture of 4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (2.45 g, 6.84 mmol) and ethyl acetate (280 mL, 0.024M) was treated with 10% palladium on carbon (0.24 g, 10% weight of starting material used). The flask was fitted with a hydrogen balloon, and the reaction stirred at 25° C. overnight. At this time, the reaction was filtered through a pad of Celite®, rinsed with ethyl acetate, and concentrated in vacuo. Flash chromatography (AnaLogix Intelliflash 280, 80 g silica gel column, 1-20% ethyl acetate/hexanes) afforded 4-[3-oxo-3-(2-phenylamino-pyridin-3-yl)-propyl]-benzoic acid methyl ester (2.00 g, 81%) as an orange solid.

Aufarbeitung

filtrationAt this time, the reaction was filtered through a pad of Celite®
washrinsed with ethyl acetate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-b886983bfb8b45408822e97ad081af14
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08471027B2

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