Potassium Phosphate, Tribasic → Methyl 2-chloro-5-methylnicotinate

HRID 2382173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382173
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:21]B(O)O.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:5]1[N:4]=[CH:3][C:2]([CH3:21])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 139377Methylboronic AcidHCID 2763343Methyl 5-bromo-2-chloronicotinate

Produkt 1

HCID 11636946Methyl 2-chloro-5-methylnicotinateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 22272177Toluene waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of methyl 5-bromo-2-chloronicotinate (1.05 g, 4.19 mmol), K3PO4 (2.95 g, 13.90 mmol), methylboronic acid (0.32 g, 5.26 mmol) and tricyclohexylphosphine (0.11 g, 0.39 mmol) in toluene/water (16 ml/0.8 ml) under nitrogen atmosphere was added Pd(OAc)2 (0.04 g, 0.18 mmol). The mixture was heated at 100° C. overnight under nitrogen atmosphere. The reaction mixture was then cooled to room temperature and concentrated in vacuum. Ethyl acetate was added to the residue and this organic layer was washed with water, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum to yield the desired product as a yellow oil. Yield=87%

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuum
  3. additionEthyl acetate was added to the residue
  4. washthis organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fed20cce1bcf4d6db64c93351143fcf6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258308B2

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