1,4-Dioxane → 1-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

HRID 132606

Reaktionsgleichung

Reaktionsgleichung von HRID 132606
[NH2:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[Cu][C:22]#[N:23].[O:24]1[CH2:29]COCC1>[C-]#N.C([N+](CC)(CC)CC)C.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:3]1[C:2]([NH:1][C:29]([NH:23][C:22]2[CH:14]=[CH:13][C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:16]=2)=[O:24])=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)([CH3:20])([CH3:19])[CH3:18]

Komponenten

8

Edukt 3

HCID 312751,4-DioxaneHCID 685300435-Amino-6-(2-tert-butylphenoxy)nicotinonitrileHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 115540381-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 3014735Tetraethylammonium cyanideKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

5-Amino-6-(2-tert-butylphenoxy)nicotinonitrile: A mixture of 63c (676 mg, 2.1 mmol), copper (1) cyanide (755 mg, 8.4 mmol), tris(dibenzilideneacetone)dipalladium(0) (77 mg, 0.08 mmol), bis(diphenylphosphino)ferrocene (187 mg, 0.34 mmol) and tetraethylammonium cyanide (330 mg, 2.1 mmol) in dioxane (11 mL) was heated at 105° C. overnight. The mixture was cooled to rt, diluted with ether (50 mL), filtered through Celite® and silica (3 g) and concentrated to give a brown solid (883 mg). The solid was purified by SiO2 chromatography (40 g) to afford 63d (472 mg. 84% yield) as a yellow solid; HPLC purity 95%, 3.37 min (Method A); [M+H]+=268.15; 1H NMR (CDCl3) δ ppm: 1.35 (s, 9 H) 4.26 (s, 2 H) 6.95 (d, J=7.70 Hz, 1 H) 7.15 (s, 1 H) 7.20 (t, J=7.70 Hz, 1 H) 7.25 (t, J=7.42 Hz, 1 H) 7.47 (d, J=7.70 Hz, 1 H) 7.82 (s, 1 H); 13C NMR (CDCl3) δ ppm: 154.22, 151.27, 141.40, 139.75, 131.98, 127.57, 127.03, 125.53, 123.53, 121.69, 117.38, 104.08, 34.60, 30.47.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite® and silica (3 g)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-901db812d251499d9e832bd475385333
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388021B2

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