Potassium Carbonate → 6-(3-Chloro-phenyl)-5-methyl-pyridine-2-carboxylic acid

HRID 632047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632047
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:18]1[N:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[CH:20][C:19]=1[CH3:27]>O.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>[Cl:1][C:2]1[CH:3]=[C:4]([C:18]2[N:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[CH:20][C:19]=2[CH3:27])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 717210026-Bromo-5-methylpyridine-2-carboxylic acid

Produkt 1

HCID 710878026-(3-Chloro-phenyl)-5-methyl-pyridine-2-carboxylic acidAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-Chlorophenylboronic acid (CAN 63503-60-6, 0.61 g, 3.9 mmol), 1,1′-bis(diphenyl-phosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 53 mg, 0.065 mmol) and potassium carbonate (CAN 584-08-7, 0.54 g, 3.9 mmol) was added to a solution of 6-bromo-5-methyl-pyridine-2-carboxylic acid (0.7 g, 3.2 mmol) in water (30 mL). The mixture was stirred at 100° C. overnight. The reaction mixture was adjusted to pH=3 and the mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated in vacuo to give product (0.55 g, 56.9%); MS (EI): m/e 248.1 [M+H]+.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f92213cc6cfe4c6e90300f37e1e0ace8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

Notizen zur Reaktion

Wird geladen…