Acetamide → N-(6-chloro-4-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)acetamide

HRID 2089007

Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[C:27]([NH2:30])(=[O:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:26][C:4]1[N:3]=[C:2]([NH:30][C:27](=[O:29])[CH3:28])[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

A mixture of Example 7a (1.44 g, 3.57 mmol), acetamide (0.295 g, 4.99 mmol), cesium carbonate (1.743 g, 5.35 mmol), palladium (II) acetate (0.024 g, 0.107 mmol), and Xantphos (0.093 g, 0.161 mmol) was degassed and heated at 85° C. in a sealed vial for 6 hours. The reaction mixture was cooled and concentrated. The residue was treated with 20% brine and extracted with EtOAc (2×). The organic layers were dried, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (90:10) to give 0.384 g of the title compound.

Aufarbeitung

temperatureThe reaction mixture was cooled
concentrationconcentrated
additionThe residue was treated with 20% brine
extractionextracted with EtOAc (2×)
customThe organic layers were dried
concentrationconcentrated
custompurified on a 40 g column
washeluting with CH2Cl2/EtOAc (90:10)

Quellen und Nachweise

ORD-Eintrag: ord-9cf9dd06848645bfa34fc70ecf343d49
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08435980B2

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