2-(4-Bromo-3,5-dimethoxyphenyl)furan → 1-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyethanone

HRID 56522Notes

Reaction equation

HRID 56522 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][C:3]=1[O:15][CH3:16].[CH2:17]([C:19]1[O:23][C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]([O:37][CH3:38])[C:31](N(OC)C)=[O:32])=[CH:26][CH:25]=2)=[N:21][N:20]=1)[CH3:18]>>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[O:11][C:12]([C:31](=[O:32])[CH:30]([C:27]3[CH:28]=[CH:29][C:24]([C:22]4[O:23][C:19]([CH2:17][CH3:18])=[N:20][N:21]=4)=[CH:25][CH:26]=3)[O:37][CH3:38])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[O:15][CH3:16]

Participants

3

Reactant 2

HCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furanHCID 584321352-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide

Product 1

HCID 584320261-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyethanoneYield 12%

Procedure

The method used for the final coupling step of Example 12 was followed for the reaction of 2-(4-bromo-3,5-dimethoxyphenyl)furan with 2-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide. Purification by chromatography (20-100% EtOAc-hexanes) gave 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyethanone as a yellow foam (0.037 g, 12% yield). MS: m/z 527.1 [M+H]+.

Workup

  1. customPurification by chromatography (20-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b315659b4157460e9add7862db887ed6
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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