Ethyl Acetate → N-(2-Bromo-pyridin-3-yl)-N-methyl-4-(4-trifluoromethoxy-phenoxy)-benzenesulfonamide

HRID 1716283Notes

Reaction equation

[Br:1][C:2]1[C:7]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[F:26][C:27]([F:37])([F:36])[O:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1.CCOC(C)=O>CC(N(C)C)=O>[Br:1][C:2]1[C:7]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:35][C:32]3[CH:33]=[CH:34][C:29]([O:28][C:27]([F:26])([F:36])[F:37])=[CH:30][CH:31]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of N-(2-bromo-pyridin-3-yl)-4-fluoro-N-methyl-benzenesulfonamide (0.1 g, 0.28 mmol) from Step B in dimethylacetamide (2 ml) was added K2CO3 (0.08 g, 1.0 mmol) and 4-trifluoromethoxyphenol (0.051 g, 0.28 mmol). The mixture was microwaved/heated at 130° C. (PMAX 130 on CEM Reactor) for 15 minutes. The reaction mixture was diluted EtOAc and washed with saturated NaCl and water. The organic phase was dried over sodiumsulfate and concentrated. The crude was purified through chromatography (20-50% EtOAc in hexanes) MS 502.6 (M+H)+

Workup

washwashed with saturated NaCl and water
dry with materialThe organic phase was dried over sodiumsulfate
concentrationconcentrated
customThe crude was purified through chromatography (20-50% EtOAc in hexanes) MS 502.6

Sources & evidence

ORD record: ord-e070c92851f64918bfe2c837a6236aa4
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803793B2

Reaction notes

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