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

HRID 1028315ノート

反応式

HRID 1028315 の反応式
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

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 66053N,N-DimethylethylenediamineHCID 71253947HCID 71253947、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-80c73f41004e48f7ae5e7c2cf85f6afa
出典データセット
uspto-grants-2014_05
特許番号
US08735440B2

反応ノート

読み込み中…