N-((1,1'-Biphenyl)-4-yl)-N-(4-bromophenyl)(1,1'-biphenyl)-4-amine → [4-(8,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylen-3-yl)-phenyl]diphenylamine

HRID 1472512Notes

Reaction equation

HRID 1472512 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.[C:26]1(C2C=CC=CC=2)[CH:31]=[CH:30][C:29]([N:32]([C:40]2[CH:45]=[CH:44][C:43](C3C=CC=CC=3)=[CH:42][CH:41]=2)[C:33]2[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=2)=[CH:28][CH:27]=1>>[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]([C:43]5[CH:42]=[CH:41][C:40]([N:32]([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[C:29]6[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=6)=[CH:45][CH:44]=5)[CH:19]=[CH:18][C:9]=42)=[CH:6][CH:5]=[CH:4][C:3]1=3

Participants

3

Reactant 2

HCID 11454354N-((1,1'-Biphenyl)-4-yl)-N-(4-bromophenyl)(1,1'-biphenyl)-4-amineHCID 672019818,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid

Product 1

HCID 86670685[4-(8,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylen-3-yl)-phenyl]diphenylamine

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 52 g (110 mmol) of bis-biphenyl-4-yl(4-bromophenyl)amine. The residue is recrystallised from toluene and from CH2Cl2/isopropanol and finally sublimed in a high vacuum. Yield: 65 g (95 mmol), 88% of theory, purity according to HPLC 99.9%.

Workup

  1. customThe residue is recrystallised from toluene and from CH2Cl2/isopropanol

Sources & evidence

ORD record
ord-a7e6e90fff1d4e6a8736284f187bc874
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

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