Potassium Carbonate → HCID 90423530, compound

HRID 1050150Notes

Reaction equation

HRID 1050150 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22]1[CH:26]=[CH:25][NH:24][N:23]=1>CN(C=O)C.C(Cl)Cl>[CH3:21][C:22]1[CH:26]=[CH:25][N:24]([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)[N:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 152724001-Fluoro-3-nitro-5-(trifluoromethyl)benzeneHCID 178428694HCID 178428694, compound

Product 1

HCID 90423530HCID 90423530, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-fluoro-3-nitro-5-(trifluoromethyl)benzene (500 mg, 2.391 mmol) and K2CO3 (496 mg, 3.59 mmol) in DMF (10 mL) was added 3-methyl-1H-pyrazole (196 mg, 2.391 mmol) in one portion. Then the mixture stirred under N2 was heated to 110° C. and reacted for 15 h. LCMS analysis showed the starting material disappeared. The solvent was removed in vacuo and the residue obtained was dissolved in DCM (40 mL) and washed with H2O (15 mL) and brine (15 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give a residue which was purified by silica column chromatography (PE/EA=8/1 to 3/1) to afford pure product 3-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole (300 mg, 1.007 mmol, 42.1% yield). 1H NMR (400 MHz, CD3OD): δ 8.84 (s, 1H), 8.47 (s, 1H), 8.41 (d, J=2.4 Hz, 1H), 8.35 (s, 1H), 6.42 (d, J=2.4 Hz, 1H), 2.36 (s, 3H). ES-LCMS: m/z 272.0 (M+H).

Workup

  1. customreacted for 15 h
  2. customThe solvent was removed in vacuo
  3. customthe residue obtained
  4. washwashed with H2O (15 mL) and brine (15 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified by silica column chromatography (PE/EA=8/1 to 3/1)

Sources & evidence

ORD record
ord-18bf8473edd94070afc4855b15edece1
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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