N-methyl-2-pyrrolidone → 2-Chloro-6-(3-fluorobenzylamino)isonicotinonitrile

HRID 1623303

Reaktionsgleichung

Reaktionsgleichung von HRID 1623303
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[N:9]=1)[C:5]#[N:6].CN1C(=O)CCC1.[F:18][C:19]1[CH:20]=[C:21]([CH2:25][NH2:26])[CH:22]=[CH:23][CH:24]=1>CCOC(C)=O>[Cl:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([NH:26][CH2:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[CH:20]=2)[N:9]=1)[C:5]#[N:6]

Komponenten

5

Edukt 3

HCID 13387N-methyl-2-pyrrolidoneHCID 668533-FluorobenzylamineHCID 7359062,6-Dichloroisonicotinonitrile

Produkt 1

HCID 830730972-Chloro-6-(3-fluorobenzylamino)isonicotinonitrileAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a scintillation vial containing 2,6-dichloroisonicotinonitrile (500 mg, 2.89 mmol) was added NMP (6 ml) and (3-fluorophenyl)methanamine (868 mg, 6.94 mmol). The homogenous reaction mixture was capped and heated to 110° C. in a oil bath for 1 hr. The reaction mixture was diluted with EtOAc and washed with sat NaHCO3, H2O and sat NaCl. The organic layer was dried Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography on silica gel (0-20% EtOAc/Hexane) to give 2-chloro-6-(3-fluorobenzylamino)isonicotinonitrile (750 mg, 95%). LCMS (m/z): 262.0 (MH+), retention time=1.03 min.

Aufarbeitung

  1. customThe homogenous reaction mixture was capped
  2. washwashed
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by column chromatography on silica gel (0-20% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6c7464a741764d19bed1d92da871493a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778951B2

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