Triethylamine → HCID 24785738, compound

HRID 1428996Notes

Reaction equation

HRID 1428996 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([F:12])[C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([S:19]([C:21]([F:24])([F:23])[F:22])=[O:20])[C:15]([C:25]([NH2:27])=O)=[N:14]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([F:12])[C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([S:19]([C:21]([F:24])([F:22])[F:23])=[O:20])[C:15]([C:25]#[N:27])=[N:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86699906HCID 86699906, compound

Product 1

HCID 24785738HCID 24785738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-Chloro-6-fluoro-4-trifluoromethyl-phenyl)-5-methyl-4-trifluoromethanesulfinyl-1H-pyrazole-3-carboxylic acid amide (0.98 g) in dichloromethane (5 mL) was added triethylamine (0.63 g, 6.2 mmol) followed by trifluoroacetic anhydride (0.89 g, 4.2 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 3 h and quenched by addition of water (2.0 mL) at 0° C. The resulting mixture was extracted with dichloromethane after it was warmed to room temperature. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography, elution with heptanes/EtOAc, to provide 1-(2-Chloro-6-fluoro-4-trifluoromethyl-phenyl)-5-methyl-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile as a white solid (0.85 g, 2.0 mmol, 99% in three steps). 1H NMR (400 MHz, CDCl3) δ ppm 2.45 (s, 3H), 7.55-7.63 (m, 1H), 7.76 (s, 1H). 19F NMR (376 MHz, CDCl3) δ ppm −113.3 (d, J=7.9 Hz, 0.5F), −113.0 (d, J=7.9 Hz, 0.5F), −73.9 (s, 1.5F), −73.8 (s, 1.5F), −63.9 (s, 3F).

Workup

  1. customquenched by addition of water (2.0 mL) at 0° C
  2. extractionThe resulting mixture was extracted with dichloromethane after it
  3. temperaturewas warmed to room temperature
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography, elution with heptanes/EtOAc

Sources & evidence

ORD record
ord-d313e421756645c5bda3acb24c2ea1fd
Source dataset
uspto-grants-2015_01
Patent number
US08937185B2

Reaction notes

Loading…