2-(3,5-Dimethoxy-4-methylphenyl)furan → 1-(5-(3,5-Dimethoxy-4-methylphenyl)furan-2-yl)-2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)ethanone

HRID 56534Notes

Reaction equation

HRID 56534 reaction equation
CON(C)[C:4](=[O:20])[CH:5]([O:18][CH3:19])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([CH3:17])=[N:15][N:16]=2)=[CH:8][CH:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)[CH:27]=[C:28]([O:31][CH3:32])[C:29]=1[CH3:30]>>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:33]2[O:34][C:35]([C:4](=[O:20])[CH:5]([O:18][CH3:19])[C:6]3[CH:7]=[CH:8][C:9]([C:12]4[O:13][C:14]([CH3:17])=[N:15][N:16]=4)=[CH:10][CH:11]=3)=[CH:36][CH:37]=2)[CH:27]=[C:28]([O:31][CH3:32])[C:29]=1[CH3:30]

Participants

3

Reactant 2

HCID 584320242-(3,5-Dimethoxy-4-methylphenyl)furanHCID 58432086N,2-dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide

Product 1

HCID 584320111-(5-(3,5-Dimethoxy-4-methylphenyl)furan-2-yl)-2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)ethanoneYield 29%

Procedure

N,2-Dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide was reacted with 2-(3,5-dimethoxy-4-methylphenyl)furan according to the procedure used for the synthesis of Example 12. Purification by chromatography (EtOAc-hexanes) gave 1-(5-(3,5-dimethoxy-4-methylphenyl)furan-2-yl)-2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)ethanone as a yellow foam (0.148 g, 29% yield). MS: m/z 449.2 [M+H]+.

Workup

  1. customused for the synthesis of Example 12
  2. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-7cc972498bfe4cae96e71c95dd172970
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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