Water → Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662450

Reaktionsgleichung

Reaktionsgleichung von HRID 1662450
Br[C:2]1[C:3](=[O:8])[CH2:4][CH2:5][C:6]=1[CH3:7].[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:19]=1B1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC.C1COCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:19]=1[C:2]1[C:3](=[O:8])[CH2:4][CH2:5][C:6]=1[CH3:7]

Komponenten

9

Edukt 5

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 44370092-Bromo-3-methyl-2-cyclopenten-1-oneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57706776Methyl 2'-fluoro-5'-(methyloxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-carboxylate

Produkt 1

HCID 57705608Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A screw-cap vial was charged with 2-bromo-3-methyl-2-cyclopenten-1-one (available from Aldrich) (0.68 g, 3.9 mmol), 66.56A (1.00 g, 2.6 mmol), potassium phosphate (1.6 g, 7.8 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (available from Aldrich) (0.33 g, 0.80 mmol), palladium(II) acetate (available from Aldrich) (0.058 g, 0.26 mmol), degassed THF (17 mL), and water (0.23 mL, 13 mmol). The mixture was purged three times with N2, stirred for 48 hours at room temperature under N2, filtered through silica gel (EtOAc), and concentrated. Trituration of the crude residue with ether afforded 66.56B (0.72 g, 78% yield) as a pale yellow solid.

Aufarbeitung

  1. customThe mixture was purged three times with N2
  2. filtrationfiltered through silica gel (EtOAc)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ef89c3da17274987b46d8285859673b9
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

Verknüpfte Notizen

Wird geladen…