2-(4-Bromo-3,5-dimethoxyphenyl)furan → 1-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(quinolin-5-yl)ethanone

HRID 56530Notes

Reaction equation

HRID 56530 reaction equation
CON(C)[C:4](=[O:18])[CH:5]([O:16][CH3:17])[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.[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][CH:13]=[C:12]4[C:7]=3[CH:8]=[CH:9][CH:10]=[N:11]4)=[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 58432006N,2-dimethoxy-N-methyl-2-(quinolin-5-yl)acetamide

Product 1

HCID 584321321-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(quinolin-5-yl)ethanoneYield 46%

Procedure

1-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(quinolin-5-yl)ethanone was synthesized from N,2-dimethoxy-N-methyl-2-(quinolin-5-yl)acetamide and 2-(4-bromo-3,5-dimethoxyphenyl)furan following the procedure used for the synthesis of Example 12. Purification by chromatography (EtOAc-hexanes) provided 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(quinolin-5-yl)ethanone as a light yellow foam (0.102 g, 46% yield). MS: m/z 482.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-e411d431b5ee42fb9c1aec2198c587be
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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