Potassium Phosphate, Tribasic → [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester

HRID 1784842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784842
[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:8]=[C:7](Br)[CH:6]=1.CC1(C)C(C)(C)OB([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][N:33]3[Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)C1C=CC=CC=1C1C=CC=CC=1N(C)C>[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[CH:6]=[C:7]([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][N:33]3[Si:38]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:39]([CH3:40])[CH3:41])[CH:8]=[C:9]([C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:10]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 50994354[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester

Produkt 1

HCID 50994359[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl esterAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178482708HCID 178482708, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester (316 mg, 0.94 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.377 mg, 0.94 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (53 mg, 0.094 mmol) were dissolved in dioxane (6 mL) under nitrogen. Aqueous 2M K3PO4 (1 mL, 1.2 mmol) was added and the mixture was heated at reflux overnight. The reaction mixture was filtered through Celite® and the solvent was removed. The product was chromatographed to give 0.350 g (70% yield) of [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite®
  4. customthe solvent was removed
  5. customThe product was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-44a512c93d614393a6546052294ee94c
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504401B2

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