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 2359172Notes

Reaction equation

HRID 2359172 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-1d97c195f73b44c9a737b565c778a7ec
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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