Sodium Carbonate → Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoate

HRID 2196752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196752
Br[C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.O.C(O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=2[CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)=[CH:29][CH:28]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 16109102Ethyl 4-(4-(2-Bromobenzyl)piperazin-1-yl)benzoate

Produkt 1

HCID 16109105Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 86587095Dimethoxyethane ethanol waterLösungsmittel

Versuchsvorschrift

A suspension of EXAMPLE 4B (13.83 g, 34.3 mmol), 4-chlorophenylboronic acid (7.04 g, 45.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.481 g, 0.686 mmol, 2 mol %) and aqueous 2M Na2CO3 (22.5 mL, 45.0 mmol) in dimethoxyethane/H2O/ethanol (7:3:2, 200 mL) was heated at 90° C. for 4.5 hours and diluted with ethyl acetate (200 mL). The layers were separated and the organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient from 5%-40% ethyl acetate/hexanes to give the desired product.

Aufarbeitung

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient from 5%-40% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-df6b6f30031443debf106d95d65129c4
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338466B2

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