Cyanide → Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

HRID 71041

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HRID 71041 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].[C-]#N.[CH3:18][N:19](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1COCC1>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:18]#[N:19])[CH:3]=2)[NH:7][CH:6]=1

참가 물질

6

반응물 3

HCID 5975CyanideHCID 6228DimethylformamideHCID 3602525-Bromo-N,N-Dimethyltryptamine

생성물 1

HCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-수율 84%

시약·촉매·용매 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 8028Tetrahydrofuran용매

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온도
110 °C

실험 절차

Under an inert atmosphere a flask is charged with [2-(5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine (Example 3) (1.0 g, 3.74 mmol), zink cyanide (0.235 g, 2 mmol), Pd2(dba)3xCHCl3 (0.194 mg, 5 mol %), dppf (bis-diphenylphosphino ferrrocene) (0.207 g, 0.374 mmol, 10 mol %), and DMF (12 mL). The orange slurry is heated to 110° C. and stirred for 21 hours. To the black suspension which has formed, THF (100 mL) is added, and this is extracted with 1 N NaOH (100 mL). The organic layer is washed with water twice (50 mL each), dried and removal of the solvent gives the title product (0.67 g, 84%) as brown solid.

후처리

  1. customTo the black suspension which has formed
  2. extractionthis is extracted with 1 N NaOH (100 mL)
  3. washThe organic layer is washed with water twice (50 mL each)
  4. customdried
  5. customremoval of the solvent

출처 및 근거

ORD 기록
ord-ace231b6097c4b76adff4768199da957
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822702B2

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