Cesium carbonate → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

HRID 505922Notes

Reaction equation

HRID 505922 reaction equation
C1(N)(N)CCCCC1.Br[C:10]1[CH:11]=[C:12]([NH2:20])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.[CH3:21][C:22]1[N:23]=[CH:24][NH:25][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.COCCOCCOC>[CH3:21][C:22]1[N:23]=[CH:24][N:25]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([NH2:20])[CH:11]=2)[CH:26]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 17842493Cyclohexane-1,1-diamineHCID 178418800HCID 178418800, compound

Product 1

HCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8150DiglymeSolvent

Procedure

To a single neck flask fitted with a condenser are added CuI (89.5 mg, 0.47 mmol), cyclohexanediamine (107.3 mg, 0.94 mmol) and diglyme (10 mL). The mixture is stirred for 10 minutes at ambient temperature. To the purple heterogeneous mixture, 3-bromo-5-trifluoromethyl-phenylamine (XVI) (1.13 g, 4.7 mmol), 4-methyl-1H-imidazole (0.77 g, 9.4 mmol) and Cs2CO3 (1.53 g, 4.7 mmol) are added. The mixture is heated at 150° C. and stirred for an additional 24 hours. The mixture is cooled to 25° C. and purified by column chromatography (silica gel; EtOAc/MeOH 95:5) to afford (I) as the major product (840 mg).

Workup

  1. customTo a single neck flask fitted with a condenser
  2. temperatureThe mixture is heated at 150° C.
  3. stirringstirred for an additional 24 hours
  4. temperatureThe mixture is cooled to 25° C.
  5. custompurified by column chromatography (silica gel; EtOAc/MeOH 95:5)

Sources & evidence

ORD record
ord-a2811b7b5e104c60ba6f7934b25ea68e
Source dataset
uspto-grants-2010_08
Patent number
US07781597B2

Reaction notes

Loading…