Imidazole → 6-Benzenesulphonylmethyl-3-(imidazol-1-yl)-2-methoxybenzoic acid

HRID 2177686Notes

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(=NO)C1C(=CC=CC=1)O.[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[Cu-]=O.C(OCC)(=O)C>[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:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Intermediate 133, 0.20 g), copper (I) oxide (0.008 g), salicylaldoxime (0.032 g), imidazole (0.08 g), cesium carbonate (0.5 g) in acetonitrile (4 ml) was sealed under nitrogen in a microwave vial and heated at 160° C. for 1 hour. After cooling, ethyl acetate was added and the solid was filtered off. The filtrate was evaporated to dryness and the residue was purified by HPLC, eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 20-98% to give 6-benzenesulphonylmethyl-3-(imidazol-1-yl)-2-methoxybenzoic acid as a white solid.

Workup

customwas sealed under nitrogen in a microwave vial
temperatureAfter cooling
filtrationthe solid was filtered off
customThe filtrate was evaporated to dryness
customthe residue was purified by HPLC
washeluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 20-98%

Sources & evidence

ORD record: ord-7c1c454f633147a381d01933514f2e90
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

Loading…