Potassium Iodide → 9-(2-hydroxy-2-methyl-3-phenoxypropyl)-9H-carbazole-3,6-dicarbonitrile

HRID 1028315노트

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HRID 1028315 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17]([CH3:27])([OH:26])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[C-:28]#[N:29].[Na+].[I-].[K+].[CH3:33][N:34](C)CCN>[Cu](I)I.C1(C)C=CC=CC=1>[OH:26][C:17]([CH3:27])([CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:16][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([C:33]#[N:34])=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][CH:3]=[C:2]([C:28]#[N:29])[CH:14]=2

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 66053N,N-DimethylethylenediamineHCID 71253947HCID 71253947, 화합물

생성물 1

HCID 712540929-(2-hydroxy-2-methyl-3-phenoxypropyl)-9H-carbazole-3,6-dicarbonitrile수율 34%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

An oven dried vial was charged with 1-(3,6-dibromo-9H-carbazol-9-yl)-2-methyl-3-phenoxypropan-2-ol (79.5 mg, 0.16 mmol), copper iodide (16 mg, 0.08 mmol), sodium cyanide (22 mg, 0.45 mmol) and potassium iodide (16 mg, 0.10 mmol). The sealed vial was nitrogen filled and evacuated three times before addition of N, N-dimethyl-1,2-ethanediamine (22.5 μl, 0.21 mmol) and anhydrous toluene (75 μl). The reaction was heated at 100° C. over 60 hours. The cooled mixture was diluted with EtOac, washed with water and brine. The organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified on silica gel in 40% THF/hexanes. Yield=34%.

후처리

  1. customAn oven dried vial
  2. additionfilled
  3. customevacuated three times
  4. additionThe cooled mixture was diluted with EtOac
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customcondensed
  9. customThe crude mixture was purified on silica gel in 40% THF/hexanes

출처 및 근거

ORD 기록
ord-80c73f41004e48f7ae5e7c2cf85f6afa
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735440B2

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