9-(4-Bromophenyl)carbazole → 3-(4-Carbazol-9-ylphenyl)-8,8-dimethyl-8H-10,12b-diazabenzo[a]-aceanthrylene

HRID 1472513Notes

Reaction equation

[CH3:1][C:2]1([CH3:25])[C:16]2[C:11](=[CH:12][CH:13]=[N:14][CH:15]=2)[N:10]2[C:17]3[C:7]([C:8]4[CH:21]=[C:20](B(O)O)[CH:19]=[CH:18][C:9]=42)=[CH:6][CH:5]=[CH:4][C:3]1=3.Br[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:45]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:39]3[C:34]2=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:29][CH:28]=1>>[CH:35]1[C:34]2[N:33]([C:30]3[CH:31]=[CH:32][C:27]([C:20]4[CH:19]=[CH:18][C:9]5[N:10]6[C:17]7[C:7]([C:8]=5[CH:21]=4)=[CH:6][CH:5]=[CH:4][C:3]=7[C:2]([CH3:25])([CH3:1])[C:16]4[C:11]6=[CH:12][CH:13]=[N:14][CH:15]=4)=[CH:28][CH:29]=3)[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]=2[CH:38]=[CH:37][CH:36]=1

Participants

Reactant 2

HCID 223613909-(4-Bromophenyl)carbazole

HCID 672019818,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid

Product 1

HCID 706653613-(4-Carbazol-9-ylphenyl)-8,8-dimethyl-8H-10,12b-diazabenzo[a]-aceanthrylene

Procedure

The compound is synthesised by the same procedure as Example 7 by reaction of 36 g (110 mmol) of 8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid with 35.4 g (110 mmol) of 9-(4-bromophenyl)-9H-carbazole. The residue is recrystallised from toluene and from CH2Cl2/isopropanol and finally sublimed in a high vacuum. Yield: 47 g (99 mmol), 82% of theory, purity according to HPLC 99.9%.

Workup

customThe residue is recrystallised from toluene and from CH2Cl2/isopropanol

Sources & evidence

ORD record: ord-65016fc8bc3840bda4ba3dd441c6d3f6
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012599B2

Reaction notes

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