Cesium carbonate → HCID 67113154, compound

HRID 2284309Notes

Reaction equation

HRID 2284309 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[CH:12]3)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[NH2:8][C:9]1[CH:10]=[CH:11][C:15]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:17][CH:16]=3)[CH:12]=[N:13]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 17148682HCID 17148682, compound

Product 1

HCID 67113154HCID 67113154, compoundYield 135.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-N-(1H-indazol-5-yl)benzamide (10.3 g, 40 mmol), 4-fluoronitrobenze (4.3 mL, 40 mmol) and cesium carbonate (13 g, 40 mmol) were taken up in DMSO (400 mL). The solution was heated to 100° C. and stirred for 24 h. After the solution was cooled it was diluted with water until a precipitate formed and stirred well for 5 min. Filtration gave a yellow solid, which was then washed well with water, followed by hexanes. After the solid was dried under vacuum it was taken up in ethanol and stirred at RT under nitrogen. The solution was treated with Pd(OH)2 (100 mg) and placed under a balloon of H2 gas. After stirring at RT for 24 h, the catalyst was removed via filtration through celite. The filtrate was concentrated under reduced pressure to give 9.36 g (67%) of a crude product as a yellow solid

Workup

  1. temperatureAfter the solution was cooled it
  2. customformed
  3. stirringstirred well for 5 min
  4. filtrationFiltration
  5. customgave a yellow solid, which
  6. washwas then washed well with water
  7. customAfter the solid was dried under vacuum it
  8. stirringstirred at RT under nitrogen
  9. additionThe solution was treated with Pd(OH)2 (100 mg)
  10. stirringAfter stirring at RT for 24 h
  11. customthe catalyst was removed via filtration through celite
  12. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9943b03b26da466693fbb3f574370b92
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

Loading…