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

HRID 64544

Reaction equation

HRID 64544 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-64a4c0300e1c4dfc9a5fefb5a8c9395c
Source dataset
uspto-grants-2016_09
Patent number
US09450195B2

Linked notes

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