1,4-Dioxane → Methyl 4-(2-fluoro-5-methylpyridin-4-yl)benzoate

HRID 968686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968686
[F:1][C:2]1[CH:7]=[C:6](I)[C:5]([CH3:9])=[CH:4][N:3]=1.C([CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)(O)=O.P([O-])([O-])([O-])=[O:24].[K+].[K+].[K+].[O:31]1CCOC[CH2:32]1>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:32][O:31][C:13](=[O:24])[C:14]1[CH:15]=[CH:16][C:17]([C:6]2[C:5]([CH3:9])=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 100600522-Fluoro-4-iodo-5-methylpyridineHCID 218789612-(4-Boronophenyl)acetic acid

Produkt 1

HCID 69422202Methyl 4-(2-fluoro-5-methylpyridin-4-yl)benzoateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 53485975CID 53485975Katalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

2-Fluoro-4-iodo-5-methyl-pyridine (0.90 g, 3.8 mmol), 4-carboxymethyl-phenyl boronic acid (0.72 g, 4.0 mmol), potassium phosphate (2.5 g, 11.8 mmol), and dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium (II) dichloromethane adduct (0.30 g, 0.37 mmol) were combined in a screw cap tube and 1.4-dioxane (20 mL) was added. Argon was bubbled through the reaction mixture, which was then sealed and heated to 95° C. overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to a red solid, which was purified by chromatography on silica (EtOAc 0 to 40% in hexanes) to afford 4-(2-fluoro-5-methyl-pyridin-4-yl)-benzoic acid methyl ester, 0.62 g, 2.5 mmol, 66% yield. 1H NMR 500 MHz (CDCl3): 8.05 (m, 3H), 7.33 (d, 2H), 6.74 (s, 1H), 3.90 (s, 3H), 2.15 (s, 3H).

Aufarbeitung

  1. customcap tube
  2. customArgon was bubbled through the reaction mixture, which
  3. customwas then sealed
  4. additionThe reaction mixture was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated to a red solid, which
  8. customwas purified by chromatography on silica (EtOAc 0 to 40% in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b0a490c0fb064421941dd2662e58f206
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304071B2

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