1,1'-Carbonyldiimidazole → HCID 26289073, compound

HRID 629099Notes

Reaction equation

HRID 629099 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([CH:22]=1)[C:19]([OH:21])=O.[F:24][C:25]([F:35])([F:34])[O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>CN(C=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([CH:22]=1)[C:19]([NH:31][C:30]1[CH:32]=[CH:33][C:27]([O:26][C:25]([F:24])([F:34])[F:35])=[CH:28][CH:29]=1)=[O:21]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6008484-(Trifluoromethoxy)anilineHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 26289073HCID 26289073, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Carbonyldiimidazole (1.054 g, 6.50 mmol) was added to a solution of 5-bromo-2-fluorobenzoic acid (1.129 g, 5.0 mmol) in DMF (10 mL) and the RM was stirred for 2 h at 0° C. 4-(trifluoromethoxy)aniline (1.129 g, 5.0 mmol) was added and the RM was allowed to warm up RT and stirred for 2 days. The solvent was evaporated off under reduced pressure and the residue was treated with aq. NaHCO3, stirred and filtered. The filtered material was washed with water, dissolved in EtOAc, washed with water and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 100 g, n-hexane/EtOAc 2:1) to afford the title compound as a white crystalline solid. UPLC-MS (Condition 2) tR=1.27 min, m/z=378.0/380.0 [M+H]+.

Workup

  1. temperatureto warm up RT
  2. stirringstirred for 2 days
  3. customThe solvent was evaporated off under reduced pressure
  4. additionthe residue was treated with aq. NaHCO3
  5. stirringstirred
  6. filtrationfiltered
  7. washThe filtered material was washed with water
  8. dissolutiondissolved in EtOAc
  9. washwashed with water and brine
  10. dry with materialdried over Na2SO4
  11. customthe solvent was evaporated off under reduced pressure
  12. customto give the crude product which
  13. customwas purified by flash chromatography (Silica gel column, 100 g, n-hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-1eaf200d9d384fc69d3842aa6c8a0ca1
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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