Acetone → (4-{[4-Difluoromethoxy-2-ethyl-8-fluoro-5-(2-methoxy-2-oxoethoxy) quinolin-3-yl]methyl}phenyl)boronic acid

HRID 1922125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922125
[CH3:1][O:2][C:3](=[O:39])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:35][CH:36]([F:38])[F:37])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([B:26]3[O:30]C(C)(C)C(C)(C)[O:27]3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].CC(C)=O>O>[F:38][CH:36]([F:37])[O:35][C:8]1[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([O:2][CH3:1])=[O:39])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([B:26]([OH:30])[OH:27])=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 67458783{4-Difluoromethoxy-2-ethyl-8-fluoro-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]quinolin-5-yloxy}acetic acid methyl ester

Produkt 1

HCID 67458287(4-{[4-Difluoromethoxy-2-ethyl-8-fluoro-5-(2-methoxy-2-oxoethoxy) quinolin-3-yl]methyl}phenyl)boronic acidAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of {4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]quinolin-5-yloxy}acetic acid methyl ester (0.89 g), sodium periodate (1.7 g), ammonium acetate (0.46 g), acetone (23 mL) and water (11 mL) was stirred at room temperature for 41 hours. The mixture was concentrated to low bulk under reduced pressure, and the residue was diluted with water and then extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and then concentrated under reduced pressure to afford title compound (0.70 g).

Aufarbeitung

  1. concentrationThe mixture was concentrated to low bulk under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aaf341536a954aecabf132d64a03d1b1
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173812B2

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