2-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile → 5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorobenzyl)nicotinonitrile

HRID 916940

Reaktionsgleichung

Reaktionsgleichung von HRID 916940
Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:6][C:3]=1[C:4]#[N:5].[Br-].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:30][Zn+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:7]2[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[N:9][C:2]([CH2:30][C:29]3[CH:32]=[CH:33][C:34]([F:35])=[C:27]([F:26])[CH:28]=3)=[C:3]([CH:6]=2)[C:4]#[N:5])=[CH:23][CH:22]=1

Komponenten

5

Edukt 2

HCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrileHCID 178505766HCID 178505766, Verbindung

Produkt 1

HCID 102175615-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorobenzyl)nicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a dried round bottom flask was added THF (1 mL), the product of Example 36 (0.050 g; 0.127 mmol), 3,4-diflourobenzylzinc bromide (0.27 mL of a 0.5 M solution in THF; 0.134 mmol), and tetrakis(triphenylphosphine) palladium (0) (0.008 g; 5 mol %). The reaction was evacuated and purged with nitrogen several times and stirred at 50° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and washed with saturated aq. NaHCO3 solution (3×), and brine. The organic portion was dried (Na2SO4), filtered, and concentrated in vacuo. Purification done by MPLC (silica gel; 0-10% ethyl acetate/hexane gradient) afforded the desired product: m/e=487 (M+3); Rt=4.8 min.

Aufarbeitung

  1. customThe reaction was evacuated
  2. custompurged with nitrogen several times
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aq. NaHCO3 solution (3×), and brine
  6. dry with materialThe organic portion was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-9e475539642041de812820d7645776ff
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271266B2

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