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

HRID 338444

反応式

HRID 338444 の反応式
[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

参加物

6

反応物 5

HCID 6228Dimethylformamide2 回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

生成物 1

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

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-90552355b19948d2b1ad3b1965bd6359
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

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