HCID 58431978, compound → 1-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-(morpholinomethyl)phenyl)ethanone

HRID 56542Notes

Reaction equation

HRID 56542 reaction equation
CON(C)[C:4](=[O:21])[CH:5]([O:19][CH3:20])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][CH:7]=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]>CCOC(C)=O>[Br:23][C:24]1[C:25]([O:37][CH3:38])=[CH:26][C:27]([C:32]2[O:33][C:34]([C:4](=[O:21])[CH:5]([O:19][CH3:20])[C:6]3[CH:7]=[CH:8][C:9]([CH2:12][N:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)=[CH:10][CH:11]=3)=[CH:35][CH:36]=2)=[CH:28][C:29]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 58431978HCID 58431978, compoundHCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furan

Product 1

HCID 584320591-(5-(4-Bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-(morpholinomethyl)phenyl)ethanoneYield 13%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,2-Dimethoxy-N-methyl-2-(4-(morpholinomethyl)phenyl)acetamide was coupled with 2-(4-bromo-3,5-dimethoxyphenyl)furan following the procedure of Example 12. Purification by chromatography (0-9% NH3-MeOH in CH2Cl2; 0.7 M NH3-MeOH used) gave a mixture which was digested with EtOAc at 30-40° C. After cooling to room temperature, the crystals were collected on a Büchner, rinsed with EtOAc and dried in vacuo to give 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-(morpholinomethyl)phenyl)ethanone as a white solid. A second batch was also isolated (0.125 g for two batches, 13% yield). MS: m/z 530.1 [M+H]+.

Workup

  1. customPurification by chromatography (0-9% NH3-MeOH in CH2Cl2; 0.7 M NH3-MeOH used)
  2. customgave a mixture which
  3. customthe crystals were collected on a Büchner
  4. washrinsed with EtOAc
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c5bb73fedd0243f69a9e4f7e3ab80a26
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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