Sodium Iodide → 9-(3'-iodo-[1,1'-biphenyl]-3-yl)-9H-carbazole

HRID 1424768Notes

Reaction equation

HRID 1424768 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[I-:27].[Na+].CNC1CCCCC1NC>[Cu]I.O1CCOCC1>[I:27][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 588711539-(3'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole

Product 1

HCID 903869089-(3'-iodo-[1,1'-biphenyl]-3-yl)-9H-carbazoleYield 96.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

9-(3′-bromo-[1,1′-biphenyl]-3-yl)-9H-carbazole (9.50 g, 23.85 mmol), sodium iodide (7.15 g, 47.7 mmol), copper(I) iodide (1.363 g, 7.16 mmol), and dioxane (239 ml) were added into a 500 mL 3-necked flask. N1,N2-dimethylcyclohexane-1,2-diamine (1.881 ml, 11.93 mmol) was added. The reaction mixture was heated and refluxed overnight. After completion of the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was filtered through a pad of Celite® and washed several times with DCM. The solvent are evaporated in vacuum. The crude material was purified by column chromatography using hexane and DCM (75/25) and gradually increasing DCM to a ratio of hexane/DCM 50/50. The product was further purified by trituration from methanol. 9-(3′-iodo-[1,1′-biphenyl]-3-yl)-9H-carbazole (10.2 g, 22.91 mmol, 96% yield) was obtained as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxed overnight
  3. customAfter completion of the reaction
  4. filtrationThe reaction mixture was filtered through a pad of Celite®
  5. washwashed several times with DCM
  6. customThe solvent are evaporated in vacuum
  7. customThe crude material was purified by column chromatography
  8. customThe product was further purified by trituration from methanol

Sources & evidence

ORD record
ord-e51b2b945f4a49018deab1531805da4c
Source dataset
uspto-grants-2015_01
Patent number
US08927749B2

Reaction notes

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