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Pyrazole → 6-(Benzenesulphonylmethyl)-2-methoxy-3-(pyrazol-1-yl)benzoic acid

HRID 2177680
Notes
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Reaction equation

HRID 2177680 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:29]1[CH:33]=[CH:32][CH:31]=[N:30]1.C(OCC)(=O)C>CN(C=O)C.[Cu]=O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 529139736-(Benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid2×

Product 1

HCID 529130506-(Benzenesulphonylmethyl)-2-methoxy-3-(pyrazol-1-yl)benzoic acidYield 26.9%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Intermediate 133, 0.1 g), copper (II) oxide (0.004 g), cesium carbonate (0.254 g) and pyrazole (0.018 g) in DMF (2 ml) was sealed in a microwave vial in an atmosphere of nitrogen and heated at 100° C. for 18 hours. After cooling, ethyl acetate was added, and the mixture was filtered through celite. The filtrate was evaporated to dryness and the residue was purified by HPLC, eluting with a mixture of acetonitrile and water containing 0.1% formic acid with a gradient of 40-60% to give 6-(benzenesulphonylmethyl)-2-methoxy-3-(pyrazol-1-yl)benzoic acid (0.026 g) as a white solid.

Workup

  1. customwas sealed in a microwave vial in an atmosphere of nitrogen
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through celite
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by HPLC
  6. washeluting with a mixture of acetonitrile and water containing 0.1% formic acid with a gradient of 40-60%

Sources & evidence

ORD record
ord-ead8a9b0ec9f49558567e55a8f140671
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067905B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes