Cesium carbonate → 5-Chloro-6-(3-chloro-phenyl)-pyridine-2-carboxylic acid

HRID 632060

Reaktionsgleichung

Reaktionsgleichung von HRID 632060
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[Cl:11].[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl.[Pd](Cl)Cl.CN(C=O)C>[Cl:11][C:3]1[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]=1[C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:12])[CH:18]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 665578096-Bromo-5-chloropyridine-2-carboxylic acid

Produkt 1

HCID 710876195-Chloro-6-(3-chloro-phenyl)-pyridine-2-carboxylic acidAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under nitrogen atmosphere, 6-bromo-5-chloro-pyridine-2-carboxylic acid (0.38 g, 1.6 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.33 g, 2.1 mmol), 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II) dichloride methylene chloride complex (CAN 95464-05-4, 30 mg) and cesium carbonate (CAN 534-17-8, 1.6 g, 4.8 mmol) was added into DMF (30 mL). The mixture was stirred at 80° C. overnight. After evaporation of solvents, the crude product was purified by column chromatography (silica gel, 12 g, petroleum ether/ethyl acetate 4/1 firstly, then methanol/methylene chloride 1/10) to give the title compound (0.14 g, 32%) as brown solid; MS (EI): m/e=268.0 [M+H]+.

Aufarbeitung

  1. customAfter evaporation of solvents
  2. customthe crude product was purified by column chromatography (silica gel, 12 g, petroleum ether/ethyl acetate 4/1 firstly

Quellen und Nachweise

ORD-Eintrag
ord-c6330391e26a496a8c175eb0e4642b3c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

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