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

HRID 64544

반응식

HRID 64544 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-64a4c0300e1c4dfc9a5fefb5a8c9395c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09450195B2

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