Dichloromethane → N-(4-cyanomethyl-2-methoxy-phenyl)-3-trifluoromethyl-benzamide

HRID 1818926

Reaktionsgleichung

Reaktionsgleichung von HRID 1818926
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.ClCCl.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].CCN(C(C)C)C(C)C>CCOC(C)=O.[Pd].O>[C:13]([CH2:12][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:14]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 136293172-(3-Methoxy-4-nitrophenyl)acetonitrile

Produkt 1

HCID 68423610N-(4-cyanomethyl-2-methoxy-phenyl)-3-trifluoromethyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 19.2 (0.096 mmol), and catalytic Pd/C in EtOAc (2 mL) were placed under an atmosphere of hydrogen for 3 hours. The reaction mixture was filtered, concentrated and taken on crude to the next reaction. The crude compound (0.096 mmol), dichloromethane (0.5 mL), 3-(trifluoromethyl)benzoyl chloride (1.05 mmol) and DIEA (1.10 mmol) was stirred at room temperature for 10 minutes. Water was added after which the mixture partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried, filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica gel using a gradient of EtOAc/hexanes provided N-(4-cyanomethyl-2-methoxy-phenyl)-3-trifluoromethyl-benzamide (compound 19.3) in 71%.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customtaken on crude to the next reaction
  4. custompartitioned between EtOAc and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash column chromatography on silica gel using a gradient of EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bf343513767548eaae3297953a3d71f5
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601725B2

Verknüpfte Notizen

Wird geladen…