4-Bromobenzaldehyde → HCID 43338295, compound

HRID 555252Notes

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:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.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:23]=[CH:22][C:19]([C:20]([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:21])=[CH:18][CH:17]=1

Participants

Reactant 4

HCID 707414-Bromobenzaldehyde

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

HCID 2724130Cornforth reagent

HCID 5462224Magnesium

Product 1

HCID 43338295HCID 43338295, compound

Procedure

First, magnesium was added to 1-bromo-3,4,5-trimethoxybenzene as a starting material, as shown in Reaction 6, and then 4-bromobenzaldehyde was added thereto to obtain a compound. Thus obtained compound was oxidized using PDC to obtain a Compound 21 derivative [(4-bromophenyl)(3,4,5-trimethoxyphenyl)methanone]. Using thus obtained compound as a starting material aminothiazole was introduced in the same manner as in the synthesis of Compound 516 to obtain Compound 571 in a form of a white solid.

Workup

customas shown in Reaction 6
customto obtain a compound

Sources & evidence

ORD record: ord-1862126e9fed49229808938514d23508
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053439B2

Reaction notes

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