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

HRID 56527Notes

Reaction equation

HRID 56527 reaction equation
[O:1]=[S:2]1(=[O:22])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:20][CH3:21])[C:14](N(OC)C)=[O:15])=[CH:9][CH:8]=1.[Br:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][C:25]=1[O:37][CH3:38]>>[Br:23][C:24]1[C:25]([O:37][CH3:38])=[CH:26][C:27]([C:32]2[O:33][C:34]([C:14](=[O:15])[CH:13]([C:10]3[CH:9]=[CH:8][C:7]([N:3]4[CH2:4][CH2:5][CH2:6][S:2]4(=[O:1])=[O:22])=[CH:12][CH:11]=3)[O:20][CH3:21])=[CH:35][CH:36]=2)=[CH:28][C:29]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furanHCID 584320552-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide

Product 1

HCID 584320171-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-2-methoxyethanone

Procedure

1-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-2-methoxyethanone was synthesized from 2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide and 2-(4-bromo-3,5-dimethoxyphenyl)furan following the procedure used for the synthesis of Example 12. Purification by chromatography (EtOAc-hexanes) provided Example 19 as a yellow solid (0.111 g, 37% yield). MS: m/z 550.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a99b66640d15461681499ca1b134797c
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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