Cesium carbonate → HCID 58674598, compound

HRID 1994156Notes

Reaction equation

HRID 1994156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])/[C:10](/[CH3:19])=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].Cl[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([C:32]#[N:33])[CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])/[C:10](/[CH3:19])=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:26]3[CH:31]=[CH:30][N:29]=[C:28]([C:32]#[N:33])[CH:27]=3)[CH:13]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 58674384HCID 58674384, compound

Product 1

HCID 58674598HCID 58674598, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(E)-N-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(3-hydroxyphenyl)-2-methylacrylamide (1.0 g, 2.81 mmol), 4-chloropicolinonitrile (428 mg, 3.09 mmol) and cesium carbonate (2.75 g, 8.43 mmol) were combined and stirred in DMF. The reaction mixture was heated at 100° C. overnight and then cooled to rt. The mixture was filtered to remove cesium carbonate, the collected precipitate was washed with EtOAc, and the combined filtrate was concentrated. Purification by column chromatography (SiO2, 0-80% EtOAc in hexanes) provided the title compound (883 mg). LCMS, FA: Rt=2.15 min, [MH+ 458.0].

Workup

  1. temperaturecooled to rt
  2. filtrationThe mixture was filtered
  3. customto remove cesium carbonate
  4. washthe collected precipitate was washed with EtOAc
  5. concentrationthe combined filtrate was concentrated
  6. customPurification by column chromatography (SiO2, 0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b2186a9509ec4aa4be9f74fe6ad6b612
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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