Potassium Phosphate, Tribasic → HCID 57441128, Verbindung

HRID 1517059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517059
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([CH3:10])=[CH:8][C:7](Cl)=[N:6][C:5]=1[O:12][CH3:13].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:16]([F:27])([F:26])[F:15])[CH:22]=2)=[N:6][C:5]=1[O:12][CH3:13]

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 57441127Methyl 6-chloro-2-methoxy-4-methylnicotinate

Produkt 1

HCID 57441128HCID 57441128, VerbindungAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5.75 g (26.7 mmol) of 6-chloro-2-methoxy-4-methyl-nicotinic acid methyl ester in 250 ml of DMF was added 10.13 g (53.3 mmol) of 3-trifluoromethyl-phenyl-boronic acid followed by 50.0 ml of a solution of tribasic potassium phosphate (2 M in water). Finally, 1.54 g (1.3 mmol) of tetrakis-(triphenylphosphine)-palladium was added and the reaction mixture was subsequently warmed up to 80° C. After 5 hours, it was cooled down to RT, poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/EtOAc 1:0 to 9:1) to give 8.54 g (98%) of the title compound as light yellow oil. MS: 326.1 (MH+).

Aufarbeitung

  1. temperatureit was cooled down to RT
  2. additionpoured
  3. extractionextracted twice with CH2Cl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (heptane/EtOAc 1:0 to 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-a53e97a182e24e5799f3073df820688f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227613B2

Notizen zur Reaktion

Wird geladen…