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

HRID 338444

반응식

HRID 338444 반응식
[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

참가 물질

6

반응물 5

HCID 6228Dimethylformamide2회HCID 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

생성물 1

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

반응 조건

온도
30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-90552355b19948d2b1ad3b1965bd6359
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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