2,4-Dichloro-5,7-difluoro-3-methylquinoline → 3-((4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)methyl)benzonitrile

HRID 1618664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618664
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[Br-].[C:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][Zn+])#[N:18]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([CH2:22][C:21]2[CH:20]=[C:19]([CH:26]=[CH:25][CH:24]=2)[C:17]#[N:18])[C:11]=1[CH3:12]

Komponenten

5

Edukt 2

HCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinolineHCID 178509756HCID 178509756, Verbindung

Produkt 1

HCID 672854223-((4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)methyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (500 mg, 2.016 mmol), tetrakis(triphenylphosphine)palladium(0) (233 mg, 0.202 mmol), and THF (5.04 mL). The mixture was sparged with N2, then (3-cyanobenzyl)zinc(II) bromide (0.5M in THF, 4.23 mL, 2.116 mmol) was added and the reaction stirred at 60° C. for 2 h. The reaction was then partitioned between EtOAc and water, and the organic layer washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography, eluting with a gradient of 0-15% EtOAc in hexane to give 3-((4-chloro-5,7-difluoro-3-methylquinolin-2-yl)methyl)benzonitrile. Mass Spectrum (ESI) m/e=329.0 (M+1).

Aufarbeitung

  1. customA screw cap vial
  2. customThe mixture was sparged with N2
  3. customThe reaction was then partitioned between EtOAc and water
  4. washthe organic layer washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography
  8. washeluting with a gradient of 0-15% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-8cf4396bdee742e890061360a16698de
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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