Sodium Iodide → 2-iodo-9-(pyridin-2-yl)-9H-carbazole

HRID 64544

反応式

HRID 64544 の反応式
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:4]=2[CH:3]=1.CNC1CCCCC1NC.[I-:31].[Na+].O1CCOCC1>O.[Cu]I>[I:31][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:4]=2[CH:3]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 312751,4-DioxaneHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 706548522-bromo-9-(pyridin-2-yl)-9H-carbazole

生成物 1

HCID 1214098552-iodo-9-(pyridin-2-yl)-9H-carbazole収率 83.1%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

実験手順

A 100 ml three neck round bottom flask was charged with 2-bromo-9-(pyridin-2-yl)-9H-carbazole (10.15 g, 31.4 mmol), copper(I) iodide (1.196 g, 6.28 mmol), N1,N2-dimethylcyclohexane-1,2-diamine (1.981 ml, 12.56 mmol), sodium iodide (18.83 g, 126 mmol), and Dioxane (60 ml.). The reaction mixture was then heated to reflux for 18 hours. The reaction mixture was diluted with deionized water and extracted with ethyl acetate. The organic portion was combined and subjected to column chromatography (SiO2, 50%/DCM in heptane) to yield 2-iodo-9-(pyridin-2-yl)-9H-carbazole (9.66 g, 83%).

後処理

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 18 hours
  3. extractionextracted with ethyl acetate

出典と根拠

ORDレコード
ord-64a4c0300e1c4dfc9a5fefb5a8c9395c
出典データセット
uspto-grants-2016_09
特許番号
US09450195B2

関連ノート

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