Potassium Carbonate → HCID 58408454, compound

HRID 1260279Notes

Reaction equation

HRID 1260279 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F:13][C:14]([F:24])([F:23])[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N+:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[NH:20][C:19]1[CH:21]=[CH:22][C:16]([O:15][C:14]([F:13])([F:23])[F:24])=[CH:17][CH:18]=1)[C:6]#[N:7])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 58408454HCID 58408454, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-fluoro-3-nitrobenzonitrile (500 mg, 3.01 mmol), 4-trifluoromethoxyaniline (404 μL, 3.01 mmol) and potassium carbonate (416 mg, 3.01 mmol) in DMSO (15.0 mL) were heated in a sealed tube within a microwave reactor at 120° C. for 10 min. The reaction mixture was cooled to rt and partitioned between EtOAc and water. The organic layer was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-40% EtOAc/hexanes as eluent) afforded the title compound i-1a. m/z (ES) 324 (MH)+. 1H NMR (500 MHz, CDCl3): δ 9.81 (s, 1H), 8.60 (d, 1H, J=1.9 Hz), 7.58 (dd, 1H, J=1.8, 9.1 Hz), 7.29 (m, 4H), 7.16 (d, 1H, J=8.9 Hz).

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-40% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-d2cf2abd084e484d907150893b8c8f71
Source dataset
uspto-grants-2013_06
Patent number
US08470819B2

Reaction notes

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