Water → 5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine

HRID 1966253Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[CH:3]=[C:4]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)=[CH:22][CH:21]=1)(=[O:18])=[O:19]

Participants

Conditions

Temperature: 120 °C

Procedure

5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine (2.6 mmol) is dissolved in DMF (12 ml), 4-(methylsulfonyl)phenol (3 eq.) and K2CO3 (4 eq.) is added. The reaction is heated to 120° C. in the microwave for 45 min. The reaction solution is pored into water and extracted with Methyltert.-butyl ether. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow oil in a yield of 15%. HPLC (method C): 1.65 min; LC-MS (method A): 1.534 min, 369.1 (MH+).

Workup

extractionextracted with Methyltert.-butyl ether
washThe combined organic layers are washed with brine
dry with materialdried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-cb3296d5b472423c92755a91f8274684
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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