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

HRID 2177680Notes

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

Participants

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

customwas sealed in a microwave vial in an atmosphere of nitrogen
temperatureAfter cooling
filtrationthe mixture was filtered through celite
customThe filtrate was evaporated to dryness
customthe residue was purified by HPLC
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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