Cesium carbonate → HCID 4763938, compound

HRID 585038Notes

Reaction equation

HRID 585038 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:14]=1[NH2:15])([O-:12])=[O:11].C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:10]([C:13]1[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[CH:16][C:14]=1[NH:15][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12162Benzonitrile, 4-bromo-HCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-

Product 1

HCID 4763938HCID 4763938, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

4-bromobenzonitrile (218 mg, 1.2 mmol), 2-nitro-4-(trifluoromethyl)aniline (206 mg, 1.0 mmol), Pd2dba3 (23 mg, 0.025 mmol), PCy2dmab (30 mg, 0.075 mmol), and Cs2CO3 (489 mg) are added to a round bottom flask. The flask is evacuated and filled with nitrogen two times and then left under vacuum for 5 min. After filling with nitrogen, toluene (4 mL Sureseal, degassed with nitrogen for 20 min) is added via syringe and the resultant dark red/black solution is heated to 100° C. with an oil bath. After 18 hr, the solution is cooled to room temperature and excess ethyl acetate is added. After washing with 1M HCl two times, the organic layer is washed with brine, dried over MgSO4, filtered through Celite, and concentrated to give crude material. This solid was purified by flash chromatography to afford 4-{[2-nitro-4-(trifluoromethyl)phenyl]amino}benzonitrile. The yield is 288 mg (94%).

Workup

  1. customThe flask is evacuated
  2. additionfilled with nitrogen two times
  3. customAfter filling with nitrogen, toluene (4 mL Sureseal, degassed with nitrogen for 20 min)
  4. additionis added via syringe
  5. waitAfter 18 hr
  6. temperaturethe solution is cooled to room temperature
  7. additionexcess ethyl acetate is added
  8. washAfter washing with 1M HCl two times
  9. washthe organic layer is washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered through Celite
  12. concentrationconcentrated
  13. customto give crude material
  14. customThis solid was purified by flash chromatography

Sources & evidence

ORD record
ord-fcbadba14b1f4f84b5e02251eb5301bf
Source dataset
uspto-grants-2005_08
Patent number
US06930106B2

Reaction notes

Loading…