Methylamine → 6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-(methylamino)pyridine-3-carbonitrile

HRID 13802

Reaktionsgleichung

Reaktionsgleichung von HRID 13802
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:3]=1.[NH2:25][CH3:26]>C1COCC1>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:4]1[N:3]=[C:2]([NH:25][CH3:26])[C:7]([C:8]#[N:9])=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile

Produkt 1

HCID 687190456-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-(methylamino)pyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
67 °C

Versuchsvorschrift

To 2-chloro-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carbonitrile (2.03 g) in THF (14 mL) was added H2NCH3 (13 mL, 2 M solution in THF). The reaction was heated to 67° C. in a closed vessel for 9 hours before concentrating. The product was dissolved in EtOAc and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 0% to 10% EtOAc in hexane affording the title compound. HPLC/MS: 387.8(M+1), 389.8 (M+3); Rt=4.26 min.

Aufarbeitung

  1. concentrationbefore concentrating
  2. dissolutionThe product was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel with a gradient elution of 0% to 10% EtOAc in hexane affording the title compound

Quellen und Nachweise

ORD-Eintrag
ord-8388cc3948c24d1aa622a1a5a14c0e04
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728141B2

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