Pyridine → 4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-benzoic acid methyl ester

HRID 1095972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095972
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:24])[C:10]([C:16]1[CH:17]=[CH:18][C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[CH3:25][O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:25][O:26][C:27](=[O:28])[C:29]1[CH:34]=[CH:33][C:32]([O:8][C:6]2[CH:5]=[CH:4][C:3]([CH:9]([CH3:24])[C:10]([OH:15])([C:16]3[CH:17]=[CH:18][C:19](=[O:23])[N:20]([CH3:22])[CH:21]=3)[C:11]([F:13])([F:14])[F:12])=[C:2]([Cl:1])[CH:7]=2)=[CH:31][CH:30]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 574213145-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

Produkt 1

HCID 666994974-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-benzoic acid methyl esterAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one (64 mg) in CH2Cl2 (1.5 ml) were added 4-methoxycarbonylphenyl-boronic acid (96 mg), copper-(II)-acetate (96 mg), molecular sieve and pyridine (70 mg). The mixture was stirred at room temperature under an air atmosphere with exclusion of moisture for 18 hours. The mixture was filtered, diluted with CH2Cl2 and washed with 1 M HCl. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 4:1=>0:1) to give the title compound (91 mg) as a colorless foam. MS (m/e, ISP neg. ion)=494.1 [M−H+].

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. additiondiluted with CH2Cl2
  3. washwashed with 1 M HCl
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 4:1=>0:1)

Quellen und Nachweise

ORD-Eintrag
ord-a252efcfb3ae4bda97f5c481c9c8a3d2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138189B2

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