Cesium carbonate → HCID 86728488, compound

HRID 1053181Notes

Reaction equation

HRID 1053181 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[C:7]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=2)=[O:14])=[C:11](F)[CH:10]=1)#[N:8].[F:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([O:34][CH3:35])[CH:28]=1>CN(C=O)C>[C:7]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=2)=[O:14])=[C:11]([O:33][C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][C:29]=2[O:34][CH3:35])[CH:10]=1)#[N:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27373684-Fluoro-2-methoxyphenolHCID 86728471HCID 86728471, compound

Product 1

HCID 86728488HCID 86728488, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Cs2CO3 (651.4 mg, 2.0 mmol) was added to a solution of 4-cyano-2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (51.4 mg, 0.2 mmol) and 4-fluoro-2-methoxyphenol (244 μL, 2.0 mmol) in DMF (1 mL) and the reaction was stirred at 100° C. for 1 hour. The reaction was filtered and purified by reverse phase HPLC using a gradient of acetonitrile in water (10-99%) and HCl as a modifier to yield 4-cyano-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (22) (26.8 mg, 35%). ESI-MS m/z calc. 379.10. found 380.17 (M+1)+; Retention time: 1.30 minutes (3 minutes run).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-67fddcf2539e46d7af1c4ebf7fe03f40
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

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