2,4-Dichlorophenylboric acid → 5-(2,4-Dichloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

HRID 1916539

Reaktionsgleichung

Reaktionsgleichung von HRID 1916539
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[N:6][CH:7]=1.[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1OB(O)O>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 219844772,4-Dichlorophenylboric acidHCID 690713915-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

Produkt 1

HCID 117436795-(2,4-Dichloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10340Sodium CarbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

10 mg (0.01 mmol) tetrakis-triphenylphosphane-palladium are added to a suspension of 60 mg (0.16 mmol) 5-bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine and 63 mg (0.32 mmol) 2,4-dichlorophenylboric acid in 4 mL 1,4-dioxane and 1 mL 2 M Na2CO3 solution and the reaction mixture is stirred for 1 h at 110° C. The mixture is evaporated down i. vac. and the residue is extracted twice with in each case 15 mL EtOH. The solvent is removed and the residue is purified by HPLC.

Aufarbeitung

  1. customThe mixture is evaporated down i
  2. extractionand the residue is extracted twice with in each case 15 mL EtOH
  3. customThe solvent is removed
  4. customthe residue is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ce43bbbb8e494ce2b06988513ee96b05
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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