3,4-Dimethoxystyrene → HCID 178489978, Verbindung

HRID 1881367

Reaktionsgleichung

Reaktionsgleichung von HRID 1881367
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](Br)=[CH:11][C:10]=1[C:24]1[N:25]([C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[N:35]([CH3:39])[CH:34]=[CH:33]3)[C:26]([OH:29])=[N:27][N:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[O:50][CH3:51])[CH:45]=[CH2:46].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.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].CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([CH:46]=[CH:45][C:44]2[CH:47]=[CH:48][C:49]([O:50][CH3:51])=[C:42]([O:41][CH3:40])[CH:43]=2)=[CH:11][C:10]=1[C:24]1[N:25]([C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[N:35]([CH3:39])[CH:34]=[CH:33]3)[C:26]([OH:29])=[N:27][N:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 614003,4-DimethoxystyreneHCID 81531DiisopropylethylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 178480083HCID 178480083, Verbindung

Produkt 1

HCID 178489978HCID 178489978, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A flask was charged with 5-(2,4-Bis-benzyloxy-5-bromo-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-ol (290 mg; 0.50 mmol), 3,4-dimethoxystyrene (98 mg; 0.60 mmol), tris(dibenzylideneacetone)dipalladium(0) (11 mg; 0.025 eq.), tris-tert-butylphosphine (10 mg; 0.10 eq.), diisopropylethylamine (77 mg; 0.60 mmol), and dimethylformamide (2 mL). The reaction was heated at 135° C. overnight, and then cooled. The solution was diluted with ethyl acetate (40 mL) and washed with water (3×40 mL). The organic layer was dried with sodium sulfate, evaporated, and purified by column chromatography to give 5-{2,4-bis-benzyloxy-5-[2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl}-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-ol (220 mg; 0.33 mmol).

Aufarbeitung

  1. temperaturecooled
  2. washwashed with water (3×40 mL)
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customevaporated
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-54a90fa267c84a54930fa5777ea8fac9
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318790B2

Verknüpfte Notizen

Wird geladen…