Sodium Carbonate → (6-Phenylpyridin-3-yl)acetic acid

HRID 882944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882944
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC(O)C.O.[OH-].[Na+]>[C:12]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Produkt 1

HCID 66718993(6-Phenylpyridin-3-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittelHCID 21889133Propan-2-ol--water (1/1)Lösungsmittel2×

Reaktionsbedingungen

Temperatur
67.5 °C

Versuchsvorschrift

2-chloropyridine-5-acetic acid (0.2 gm, 1.21 mmole), phenylboronic acid (0.16 gm, 1.3 mmole) and 50% water wet 10% Palladium carbon (0.08 gm, 0.036 mmole Pd) were added to 10 ml of 5:1 water isopropanol mixture, then Na2CO3 (0.15 gm, 1.4 mmole) dissolved in 3 ml of water was added to the above mixture, the reaction was heated at 65-70° C. overnight, the reaction was cooled to room temperature, diluted with 20 ml of 70:15:1 i-PrOH/H2O/10% NaOH, filtered, the catalyst was washed with 20 ml×3 using the above mixture, the filtrate was dried under vacuum and crude mixture was used without any purification in the next step.

Aufarbeitung

  1. additionwas added to the above mixture
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe catalyst was washed with 20 ml×3 using the above mixture
  5. customthe filtrate was dried under vacuum and crude mixture
  6. customwas used without any purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-1881d574544848ffb3ab7883e2206240
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236799B2

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