2-(4-Bromo-3,5-dimethoxyphenyl)furan → 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)ethanone

HRID 56541Notes

Reaction equation

HRID 56541 reaction equation
CON(C)[C:4](=[O:18])[CH:5]([O:16][CH3:17])[C:6]1[CH:15]=[CH:14][C:9]2[N:10]([CH3:13])[N:11]=[N:12][C:8]=2[CH:7]=1.[Br:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][C:24]([C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)=[CH:23][C:22]=1[O:34][CH3:35]>>[Br:20][C:21]1[C:22]([O:34][CH3:35])=[CH:23][C:24]([C:29]2[O:30][C:31]([C:4](=[O:18])[CH:5]([O:16][CH3:17])[C:6]3[CH:15]=[CH:14][C:9]4[N:10]([CH3:13])[N:11]=[N:12][C:8]=4[CH:7]=3)=[CH:32][CH:33]=2)=[CH:25][C:26]=1[O:27][CH3:28]

Participants

3

Reactant 2

HCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furanHCID 58432158HCID 58432158, compound

Product 1

HCID 584321211-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)ethanoneYield 34%

Procedure

N,2-Dimethoxy-N-methyl-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)acetamide was coupled with 2-(4-bromo-3,5-dimethoxyphenyl)furan according to the procedure for the synthesis of Example 13. Purification by chromatography provided 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)ethanone as a light yellow foam (0.153 g, 34% yield). MS: m/z 486.1 [M+H]+.

Workup

  1. customPurification by chromatography

Sources & evidence

ORD record
ord-691febb7477c4961a57f77687e052965
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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