Potassium Phosphate, Tribasic → 4-Chloro-2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

HRID 347530

Reaktionsgleichung

Reaktionsgleichung von HRID 347530
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9](B(O)O)=[CH:10][C:3]=12.I[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:10][C:3]=12

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 707143-IodopyridineHCID 21081673(4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid

Produkt 1

HCID 210816764-Chloro-2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Argon was bubbled through a mixture of 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-ylboronic acid (5.55 g, 17 mmol), 3-iodopyridine (6.97 g, 34 mmol), Pd(OAc)2, 2-dicyclohexylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (405 mg, 0.85 mmol), and K3PO4 (2 M in H2O, 34 mmol) in DME (50 mL) for 10 min and then heated at reflux overnight. The reaction mixture was diluted with EtOAc and washed with saturated aq. K2HPO4 solution. The title compound was purified by flash column chromatography (silica gel, 20% EtOAc/CH2Cl2) to afford the desired product (3.2 g, 52% yield) as an oil. LC/MS(ESI+) m/z 361 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. washwashed with saturated aq. K2HPO4 solution
  4. customThe title compound was purified by flash column chromatography (silica gel, 20% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-083f4f23d8fc443688e30f2d2eb94193
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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