5-Bromo-1,2,3-trimethoxybenzene → HCID 66987404, compound

HRID 555251Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[C:5]([O:13][CH3:14])[CH:4]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>>[Br:15][C:16]1[CH:17]=[C:18]([C:19]([C:3]2[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[C:5]([O:13][CH3:14])[CH:4]=2)=[O:20])[CH:21]=[CH:22][CH:23]=1

Participants

Reactant 4

HCID 758855-Bromo-1,2,3-trimethoxybenzene

HCID 765833-Bromobenzaldehyde

HCID 2724130Cornforth reagent

HCID 5462224Magnesium

Product 1

HCID 66987404HCID 66987404, compound

Procedure

First, magnesium was added to 1-bromo-3,4,5-trimethoxybenzene as a starting material, as shown in Reaction 6, and then 3-bromobenzaldehyde was added thereto to obtain a compound. Thus obtained compound was oxidized using PDC to obtain a Compound 21 derivative [(3-bromophenyl)(3,4,5-trimethoxyphenyl)methanone]. Thus obtained compound and thiophen-3-boronic acid were subjected to the Suzuki reaction, in the same manner as in the synthesis of Compound 457, to obtain Compound 568.

Workup

customas shown in Reaction 6
customto obtain a compound

Sources & evidence

ORD record: ord-4163dee435434a658044f944f47d78a1
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053439B2

Reaction notes

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