Cesium carbonate → 3-(6-Ethanesulfonyl-pyridin-3-yloxy)-5-methoxymethoxybenzoic acid methyl ester

HRID 2355010Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][C:21](=[O:33])[C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([O:29][CH2:30][O:31][CH3:32])[CH:23]=1.[Cl-].[NH4+]>CN(C)C=O.C(OC(=O)C)C>[CH3:19][O:20][C:21](=[O:33])[C:22]1[CH:23]=[C:24]([O:29][CH2:30][O:31][CH3:32])[CH:25]=[C:26]([O:28][C:2]2[CH:7]=[N:6][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

After adding 178 mg (0.71 mmol) of 5-bromo-2-ethanesulfonylpyridine and 232 mg (0.71 mmol) of cesium carbonate to a solution of 100 mg (0.47 mmol) of 5-hydroxy-3-methoxymethoxybenzoic acid methyl ester in N,N-dimethylformamide (1.0 ml), the mixture was stirred at 100° C. for 2.5 hours under a nitrogen atmosphere. Acetic acid ethyl ester and aqueous ammonium chloride were added to the reaction mixture, the aqueous layer was extracted with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=1:1) to obtain 165 mg of 3-(6-ethanesulfonyl-pyridin-3-yloxy)-5-methoxymethoxybenzoic acid methyl ester (yield: 91%) as a colorless oil.

Workup

extractionthe aqueous layer was extracted with acetic acid ethyl ester
washthe organic layer was washed with brine
customdried
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=1:1)

Sources & evidence

ORD record: ord-f13d8631be5b4a99a1d8f02e0f2be4b9
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754743B2

Reaction notes

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