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

HRID 338444

Reaktionsgleichung

Reaktionsgleichung von HRID 338444
[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 0.4M solution of chlormethylene 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 0.3M solution of 2-chloro-5-phenylpyrazine in DMF (0.50 mL, 0.15 mmol). 2M 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-90552355b19948d2b1ad3b1965bd6359
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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