Ethanol → 3-(Pyridin-4-yl)thieno[3,2-c]pyridin-4(5H)-one

HRID 920935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920935
Br[C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[N:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.CC(=O)OCC.O>[N:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:6]3[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=3[S:4][CH:3]=2)=[CH:23][CH:22]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

Produkt 1

HCID 866834493-(Pyridin-4-yl)thieno[3,2-c]pyridin-4(5H)-oneAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Bromothieno[3,2-c]pyridin-4(5H)-one (1000 mg, 4.35 mmol) from Example 202.3 was suspended in 2 mL of toluene and 2 mL of ethanol under argon. Then, an aqueous solution of sodiumcarbonate (691 mg, 6.52 mmol, 2 M) was added. To the suspension, pyridin-4-boronic acid (534 mg, 4.35 mmol) and then tetrakis(triphenyl phosphine)palladium(0) (502 mg, 0.435 mmol) were added. The reaction mixture was heated in a Biotage microwave at 130° C. for 30 min. Water and EA were added. The precipitate formed was collected to give 480 mg of the title compound. The filtrate was acidified with 2 M HCl and extracted with EA (twice). The aqueous phase was basified and extracted three times with EA. The organic phases were combined, washed with HCl, dried (MgSO4) and evaporated to give further 43 mg of the title compound. Total yield: 523 mg (52.4%). LC-MS: 229.1 [M+H]+; Rt: 0.427.

Aufarbeitung

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  2. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-27870fcda7434709a718caa504b32e4e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273068B2

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