8,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid → 8,8,8',8'-Tetramethyl-8H,8'H-[3,3']bi[10,12b-diazabenzo[a]aceanthrylenyl]

HRID 1472514Notes

Reaction equation

HRID 1472514 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:48]=[CH:47][C:30]2[N:31]3[C:44]4[C:43]([C:29]=2[CH:28]=1)=[CH:42][CH:41]=[CH:40][C:39]=4[C:38]([CH3:46])([CH3:45])[C:37]1[C:32]3=[CH:33][CH:34]=[N:35][CH:36]=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:27]5[CH:48]=[CH:47][C:30]6[N:31]7[C:44]8[C:43]([C:29]=6[CH:28]=5)=[CH:42][CH:41]=[CH:40][C:39]=8[C:38]([CH3:45])([CH3:46])[C:37]5[C:32]7=[CH:33][CH:34]=[N:35][CH:36]=5)[CH:19]=[CH:18][C:9]=42)=[CH:6][CH:5]=[CH:4][C:3]1=3

Participants

3

Reactant 2

HCID 672019818,8-Dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acidHCID 672021773-bromo-8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene

Product 1

HCID 706654218,8,8',8'-Tetramethyl-8H,8'H-[3,3']bi[10,12b-diazabenzo[a]aceanthrylenyl]

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 (110 mmol) of 3-bromo-8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene. The residue is recrystallised from toluene and from CH2Cl2/isopropanol and finally sublimed in a high vacuum. Yield: 50 g (88 mmol), 80% 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-f758a1bf6e6944f1bc3a80e968d146e8
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

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