Iodobenzene → HCID 12220806, compound

HRID 929284Notes

Reaction equation

HRID 929284 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[N:7]=[C:8]3[CH:20]=[C:19]4[C:11](=[N:12][C:13]5[C:18]4=[CH:17][CH:16]=[CH:15][CH:14]=5)[CH:10]=[C:9]3[C:2]=12.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C[C:29]([CH3:32])([O-])[CH3:30].[Na+].[C:34](P(C(C)(C)C)C(C)(C)C)(C)([CH3:36])[CH3:35]>CC1C=CC=CC=1C.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[C:22]1([N:7]2[C:8]3[C:9](=[CH:10][C:11]4[N:12]([C:30]5[CH:29]=[CH:32][CH:36]=[CH:34][CH:35]=5)[C:13]5[C:18]([C:19]=4[CH:20]=3)=[CH:17][CH:16]=[CH:15][CH:14]=5)[C:2]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:1]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 114764Indolo(3,2-b)carbazoleHCID 23676156Sodium t-butoxide

Product 1

HCID 12220806HCID 12220806, compoundYield 211.7%

Reagents, catalysts & solvents 2

HCID 72499888Dibenzalacetone palladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

Indolo[3,2-b]carbazole (1.20 g, 4,68 mmol) was suspended in 48 ml of o-xylene under nitrogen and treated with iodobenzene (2.10 g, 10.3 mmol) followed by the sodium t-butoxide (1.35 g, 14.0 mmol), tri-t-butylphosphine (0.15 g, 0.74 mmol) and palladium dibenzylideneacetone (0.34 g, 0.37 mmol). The resulting mixture was heated to 120° C. and stirred for 20 minutes. It was then cooled to room temperature filtered through a short pad of silica gel and the pad washed with toluene. The combined filtrates were combined and concentrated to dryness to afford a dark-colored solid. Purification using a Biotage® automated flash purification system afforded 0.640 g of N,N′-bis(phenyl)-indolo[3,2-b]carbazole with a purity of 99.7%. MP=306.5° C.; Tg=238.9° C.

Workup

  1. temperatureIt was then cooled to room temperature
  2. filtrationfiltered through a short pad of silica gel
  3. washthe pad washed with toluene
  4. concentrationconcentrated to dryness
  5. customto afford a dark-colored solid
  6. customPurification
  7. customflash purification system

Sources & evidence

ORD record
ord-25c1941aed7544d89903df545490c7ba
Source dataset
uspto-grants-2016_03
Patent number
US09293716B2

Reaction notes

Loading…