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

HRID 56536Notes

Reaction equation

HRID 56536 reaction equation
[CH:1]1([C:4]2[O:8][C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([O:22][CH3:23])[C:16](N(OC)C)=[O:17])=[CH:11][CH:10]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1.[Br:24][C:25]1[C:30]([O:31][CH3:32])=[CH:29][C:28]([C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)=[CH:27][C:26]=1[O:38][CH3:39]>>[Br:24][C:25]1[C:26]([O:38][CH3:39])=[CH:27][C:28]([C:33]2[O:34][C:35]([C:16](=[O:17])[CH:15]([C:12]3[CH:11]=[CH:10][C:9]([C:7]4[O:8][C:4]([CH:1]5[CH2:2][CH2:3]5)=[N:5][N:6]=4)=[CH:14][CH:13]=3)[O:22][CH3:23])=[CH:36][CH:37]=2)=[CH:29][C:30]=1[O:31][CH3:32]

Participants

3

Reactant 2

HCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furanHCID 584320202-(4-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide

Product 1

HCID 584320601-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyethanoneYield 31%

Procedure

2-(4-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide was reacted with 2-(4-bromo-3,5-dimethoxyphenyl)furan according to the procedure for the synthesis of Example 12. Purification by chromatography (EtOAc-hexanes) gave 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyethanone as a yellow foam (0.126 g, 31% yield). MS: m/z 539.2 [M+H]+.

Workup

  1. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-d1b4e1d807024c7aa9db382690d91548
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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