Sodium Carbonate → 2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol

HRID 1916710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916710
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]3)=[N:12][CH:13]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][CH:30]=1>O1CCOCC1.CO>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]4)=[N:12][CH:13]=2)=[CH:31][CH:30]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 673628532-[5-(5-Bromo-pyridin-2-ylethynyl)-indol-1-yl]-ethanol

Produkt 1

HCID 673637692-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Under an N2 atmosphere 56 mL 2 M Na2CO3 solution and 1.29 g (1.1 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 19.0 g (55.7 mmol) 2-[5-(5-bromo-pyridin-2-ylethynyl)-indol-1-yl]-ethanol and 11.55 g (72.4 mmol) 4-chlorophenyl-boric acid in 320 mL 1,4-dioxane and 80 mL MeOH and the reaction mixture is heated to 110° C. for 16 h. The mixture is evaporated down i. vac., the residue is combined with 300 mL water and the suspension is stirred vigorously. The precipitate is filtered off and washed with 200 mL water. The precipitate is suspended three times, each time with 600 mL PE/DCM (5:1), suction filtered and finally dried in the air until a constant weight is obtained.

Aufarbeitung

  1. customThe mixture is evaporated down i
  2. filtrationThe precipitate is filtered off
  3. washwashed with 200 mL water
  4. filtrationeach time with 600 mL PE/DCM (5:1), suction filtered
  5. customfinally dried in the air until a constant weight
  6. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-9ea2b469ed1b4fe1a1b90051c789402f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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