Cesium carbonate → (2-Isopropoxy-5-methanesulfonyl-phenyl)-[3-(4-trifluoromethyl-phenoxy)-azetidin-1-yl]-methanone

HRID 1711756Notes

Reaction equation

HRID 1711756 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=2[O:18][CH:19]([CH3:21])[CH3:20])=[O:7])[CH2:3]1.F[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:19]([O:18][C:9]1[CH:10]=[CH:11][C:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:13][C:8]=1[C:6]([N:4]1[CH2:5][CH:2]([O:1][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:3]1)=[O:7])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 58673079(3-Hydroxy-azetidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

Product 1

HCID 11510854(2-Isopropoxy-5-methanesulfonyl-phenyl)-[3-(4-trifluoromethyl-phenoxy)-azetidin-1-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.32 mmol (3-hydroxy-azetidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, 0.32 mmol 4-fluoro-benzotrifluoride and 0.96 mmol cesium carbonate in 10 ml acetonitrile was refluxed overnight. The reaction mixture was concentrated to yield the crude compound, purified by chromatography (methanol/dichloromethane). MS (m/e): 458.4 (M+H+, 100%).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-b88390a285d54d3789afd7dfc92aa49e
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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