Dimethylformamide → 6-chloro-5-(5-phenylpyrazin-2-yl)-1H-indole-3-carbaldehyde

HRID 1054787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054787
[Cl-].ClC=[N+](C)C.CN([CH:10]=[O:11])C.[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[CH:15][C:14]=1B1OCC(C)(C)CO1.Cl[C:31]1[CH:36]=[N:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][N:32]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH:10]=[O:11])=[CH:18][NH:19]2)=[CH:15][C:14]=1[C:31]1[CH:36]=[N:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][N:32]=1

Komponenten

6

Edukt 5

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 12366642-Chloro-5-phenylpyrazineHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Produkt 1

HCID 866987756-chloro-5-(5-phenylpyrazin-2-yl)-1H-indole-3-carbaldehyde

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a 0.4 M solution of chloromethylene dimethylammonium chloride in DMF (7.5 mL, 3.8 mmol) was added 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (493 mg, 1.88 mmol). The mixture was stirred at 30° C. for 2 hrs. 0.50 mL of this solution (0.15 mmol) was placed in a vial with a 0.3 M solution of 2-chloro-5-phenylpyrazine in DMF (0.50 mL, 0.15 mmol). 2 M potassium carbonate (0.30 mL, 0.60 mmol) was then added and the mixture purged with nitrogen. PddppfCl2 (9 mg, 0.01 mmol) was then added and the vial capped and heated to 90° C. for 3 hours. The reaction mixture was concentrated by Speedvac and purified via preparative TLC to give the title compound that was taken forward without further purification.

Aufarbeitung

  1. customthe mixture purged with nitrogen
  2. additionPddppfCl2 (9 mg, 0.01 mmol) was then added
  3. customthe vial capped
  4. temperatureheated to 90° C. for 3 hours
  5. concentrationThe reaction mixture was concentrated by Speedvac
  6. custompurified via preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-94fdf8a5b3ec477fa47756a874f7b333
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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