Cesium fluoride → 5-Aminobiphenyl-2-carbonitrile

HRID 501583

Reaktionsgleichung

Reaktionsgleichung von HRID 501583
Cl[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]#[N:10])[NH2:5].[F-].[Cs+].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1C(=O)CCC1.CCOC(C)=O.Cl[Pd](Cl)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)P(C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:9]([C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:10]

Komponenten

7

Edukt 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 887284-Amino-2-chlorobenzonitrile

Produkt 1

HCID 441582825-Aminobiphenyl-2-carbonitrileAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178479803HCID 178479803, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Commercially available 3-chloro-4-cyanoaniline (305 mg, 2.0 mmol) was dissolved in NMP (8 mL), and CsF (608 mg, 4.0 mmol), phenyl boronic acid (268 mg, 2.2 mmol) and dichlorobis(tricyclohexylphosphino)palladium (73 mg, 0.1 mmol) were added. The reaction was then heated to 100° C. for 16 h. After cooling to rt, the reaction mixture was taken up in EtOAc, washed with water (2×), dried (Na2SO4), concentrated under reduced pressure, and purified by silica gel flash chromatography eluting with EtOAc/hexanes (1:1) to give compound 47A (371 mg, 96%) as a yellow solid. LC/MS m/z 195 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. washwashed with water (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel flash chromatography
  6. washeluting with EtOAc/hexanes (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b4b89d34f5d54eef85433dec6ae4d613
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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