Phenethyl bromide → 1,2,3,4,5,6-Hexahydro-3,9-dimethyl-6-phenethylazepino[4,5-b]indole

HRID 1481412노트

반응식

HRID 1481412 반응식
[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3]1.N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>[Cu](I)I.O.CN(C=O)C>[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:5]=2[CH2:4][CH2:3]1

참가 물질

8

반응물 4

HCID 7666Phenethyl bromideHCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 685600921,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole

생성물 1

HCID 593683711,2,3,4,5,6-Hexahydro-3,9-dimethyl-6-phenethylazepino[4,5-b]indole

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

The title compound was prepared by following general procedure 4. 3,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (214 mg, 1.0 mmol) was taken with copper iodide (19 mg, 0.1 mmol), L-proline (23 mg, 0.2 mmol), potassium phosphate tribasic (426 mg, 2.0 mmol) and (2-bromoethyl)benzene (185 mg, 1 mmol) and DMF was added, the reaction was stirred at 90° C. under argon atmosphere for 12 h. The reaction was monitored by LCMS. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The crude so obtained was purified by column chromatography (silica gel 100-200 mesh) (gradient 5% MeOH:DCM). The pure product was converted to oxalate salt using oxalic acid and THF.

후처리

  1. additionwas added
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude so obtained
  8. customwas purified by column chromatography (silica gel 100-200 mesh) (gradient 5% MeOH:DCM)

출처 및 근거

ORD 기록
ord-140a5d9478324fa6af24d5ce6dd16853
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409910B2

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