Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(4-(1H-pyrazol-4-yl)phenyl)-1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxyethanone

HRID 512612Notes

Reaction equation

HRID 512612 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[O:14][C:13]([C:15](=[O:55])[CH:16]([O:53][CH3:54])[C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:24]=[N:25][N:26](C(C5C=CC(OC)=CC=5)(C5C=CC(OC)=CC=5)C5C=CC(OC)=CC=5)[CH:27]=4)=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:56][CH3:57].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C([O-])(O)=O.[Na+]>CO.O>[NH:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([CH:16]([O:53][CH3:54])[C:15]([C:13]3[O:14][C:10]([C:5]4[CH:4]=[C:3]([O:56][CH3:57])[C:2]([Br:1])=[C:7]([O:8][CH3:9])[CH:6]=4)=[CH:11][CH:12]=3)=[O:55])=[CH:18][CH:19]=2)[CH:27]=[N:26]1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 58432164HCID 58432164, compound

Product 1

HCID 584321022-(4-(1H-pyrazol-4-yl)phenyl)-1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxyethanoneYield 17%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a suspension of 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-(1-(tris(4-methoxyphenyl)methyl)-1H-pyrazol-4-yl)phenyl)ethanone (0.10 g, 0.12 mmol) in MeOH—H2O (22 mL, 10:1) was added pyridinium para-toluenesulfonate (0.046 g, 0.16 mmol). After stirring for 18 hrs at room temperature, saturated aqueous NaHCO3 was added and the volatiles were removed in vacuo. The residue was diluted with a small amount of H2O then extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (50-100% EtOAc-hexanes) provided 2-(4-(1H-pyrazol-4-yl)phenyl)-1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxyethanone as a yellow foam (0.010 g, 17% yield). MS: m/z 497.0 [M+H]+.

Workup

  1. customthe volatiles were removed in vacuo
  2. additionThe residue was diluted with a small amount of H2O
  3. extractionthen extracted with EtOAc
  4. washThe combined organics were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (50-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-01b940484c884c7ca6ef89a931c477cd
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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