Cesium carbonate → 5-(3,3-Dimethyl-but-1-ynyl)-3-[4-(pyridin-2-yloxy)-phenylamino]-thiophene-2-carboxylic acid methyl ester

HRID 1046411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046411
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]#[C:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[NH2:10])=[O:4].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-])[O-].[Cs+].[Cs+].Br[C:66]1[CH:78]=[CH:77][C:69]([O:70][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=2)=[CH:68][CH:67]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]#[C:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[NH:10][C:66]1[CH:67]=[CH:68][C:69]([O:70][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=2)=[CH:77][CH:78]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 232019352-(4-Bromophenoxy)pyridineHCID 24989346Methyl 3-amino-5-(3,3-dimethylbut-1-yn-1-yl)thiophene-2-carboxylate

Produkt 1

HCID 581140985-(3,3-Dimethyl-but-1-ynyl)-3-[4-(pyridin-2-yloxy)-phenylamino]-thiophene-2-carboxylic acid methyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 3-amino-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (0.200 g, 0.843 mmol), palladium acetate (0.019 g, 0.084 mmol), xantphos (0.058 g, 0.101 mmol), cesium carbonate (0.767 g, 2.36 mmol) and 2-(4-Bromo-phenoxy)-pyridine (0.252 g, 1.01 mmol) in toluene (3 mL) was heated by microwave to 110° C. for 45 minutes. The reaction was diluted with ethyl acetate filtered through a Celite pad and purified by silica gel chromatography to give 5-(3,3-Dimethyl-but-1-ynyl)-3-[4-(pyridin-2-yloxy)-phenylamino]-thiophene-2-carboxylic acid methyl ester in 66% yield.

Aufarbeitung

  1. filtrationfiltered through a Celite pad
  2. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a428230856704956bebb63561fcaae31
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569302B2

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