2-(4-Bromo-3,5-dimethoxyphenyl)furan → 1-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(6-(piperidin-1-yl)pyridin-3-yl)ethanone

HRID 56537Notes

Reaction equation

HRID 56537 reaction equation
CON(C)[C:4](=[O:20])[CH:5]([O:18][CH3:19])[C:6]1[CH:7]=[N:8][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:11]=1.[Br:22][C:23]1[C:28]([O:29][CH3:30])=[CH:27][C:26]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)=[CH:25][C:24]=1[O:36][CH3:37]>>[Br:22][C:23]1[C:24]([O:36][CH3:37])=[CH:25][C:26]([C:31]2[O:32][C:33]([C:4](=[O:20])[CH:5]([O:18][CH3:19])[C:6]3[CH:7]=[N:8][C:9]([N:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)=[CH:10][CH:11]=3)=[CH:34][CH:35]=2)=[CH:27][C:28]=1[O:29][CH3:30]

Participants

3

Reactant 2

HCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furanHCID 58432037HCID 58432037, compound

Product 1

HCID 584321571-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(6-(piperidin-1-yl)pyridin-3-yl)ethanoneYield 65%

Procedure

N,2-Dimethoxy-N-methyl-2-(6-(piperidin-1-yl)pyridin-3-yl)acetamide was reacted with 2-(4-bromo-3,5-dimethoxyphenyl)furan according to the procedure used for Example 12. Purification by chromatography (20-75% EtOAc-hexanes) gave 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(6-(piperidin-1-yl)pyridin-3-yl)ethanone as a light yellow solid (0.328 g, 65% yield). MS: m/z 515.4 [M+H]+.

Workup

  1. customPurification by chromatography (20-75% EtOAc-hexanes)

Sources & evidence

ORD record
ord-918dde5c5710408188d343518774b0eb
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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