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Water → Ethyl 3-chloro-2-methylisonicotinate

HRID 1508202
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1508202
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[C:6]=1[Cl:12])[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:14])[C:6]=1[Cl:12])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 46311339Ethyl 2,3-dichloropyridine-4-carboxylate

Produkt 1

HCID 86721905Ethyl 3-chloro-2-methylisonicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2,3-dichloroisonicotinic acid ethyl ester (3.15 mmol), K2CO3 (4.73 mmol) and trimethylboroxine (3.15 mmol) in 4 mL dioxane was degassed with Ar. Then, tetrakis(triphenylphosphine)palladium (0.31 mmol) was added and the mixture was heated to reflux overnight. At RT, the reaction mixture was poured into water and extracted with DCM. The combined organic layers were dried over K2CO3, filtered over a pad of celite and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (8/2) gives the desired product as brown oil;

Aufarbeitung

  1. customwas degassed with Ar
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over K2CO3
  6. filtrationfiltered over a pad of celite
  7. concentrationconcentrated in vacuo
  8. customPurification by CC (KP-SIL™ from Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-eff0175657f346fc9430896d99cce9be
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221832B2

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