Ammonia → Perampanel

HRID 547690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547690
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:21])[NH:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.N>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:21])[N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2]

Komponenten

9

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 223189453-(2-Cyanophenyl)-5-(2-pyridyl)-2(1H)-pyridone

Produkt 1

HCID 9924495PerampanelAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8895Cupric acetateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 0.11 g of 3-(2-cyanophenyl)-5-(2-pyridyl)-2(1H)-pyridone, 0.12 g of phenyl boronic acid 0.1 g of copper acetate and 0.3 ml of triethylamine in 10 ml of methylene chloride was stirred at room temperature for overnight. To this were added 5 ml of concentrated aqueous ammonia, 10 ml of water and 40 ml of ethyl acetate and the organic layer was separated, washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:2) to give 0.06 g of the title product as pale yellow powder.

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated saline solution and dried over magnesium sulfate
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-3405215546b04ed3bf343bd0a63e3c05
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939549B2

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