Dimethylformamide → Methyl 3-{[5-(4-cyano-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate

HRID 623883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623883
CN(C)C=O.Br[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:15])[CH:8]=1.[CH3:16][C:17]([CH3:40])([CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][N:25]=1)[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([C:27]2[C:28]([CH3:30])=[CH:29][C:24]([O:23][CH2:22][C:17]([CH3:16])([CH3:40])[C:18]([O:20][CH3:21])=[O:19])=[N:25][CH:26]=2)=[CH:8][C:9]=1[F:15])#[N:12]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 7360294-Bromo-2-fluorobenzonitrileHCID 67975267Methyl 2,2-dimethyl-3-((4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl)oxy)propanoate

Produkt 1

HCID 67973490Methyl 3-{[5-(4-cyano-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoateAusbeute 104,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

N,N-dimethylformamide (30 mL) was added to 4-bromo-2-fluorobenzonitrile (2000 mg), methyl 2,2-dimethyl-3-{[4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}propanoate (4191 mg) and palladium chloride (dppf) methylene chloride complex (408 mg), and after adding 2N aqueous sodium carbonate solution (15 mL) to the mixture, the atmosphere was replaced with nitrogen and the resulting mixture was stirred at 60° C. for 7 hours. Ethyl acetate and water were added to the reaction mixture, and the liquids were separated. The organic layer was separated, washed with a saturated brine, and the residue obtained by concentrating the mixture under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20) to obtain methyl 3-{[5-(4-cyano-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate (3587 mg).

Aufarbeitung

  1. customthe liquids were separated
  2. customThe organic layer was separated
  3. washwashed with a saturated brine
  4. customthe residue obtained
  5. concentrationby concentrating the mixture under reduced pressure
  6. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-628a36554cbc4bc5a32b391257ecc054
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302996B2

Notizen zur Reaktion

Wird geladen…