Hydrochloric Acid → HCID 178434540, compound

HRID 1488213Notes

Reaction equation

HRID 1488213 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:10]([CH3:18])=[N:9]1)C1C=CC=CC=1.Cl.[H][H]>CO.[Pd]>[CH3:18][C:10]1[C:11]([CH2:13][C:14]([F:16])([F:15])[F:17])=[CH:12][NH:8][N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 90030348HCID 90030348, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 178434540HCID 178434540, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-3-methyl-4-(2,2,2-trifluoroethyl)-1H-pyrazole (compound 314.5, 700 mg, 2.75 mmol) in methanol (10 mL) was added palladium on carbon (700 mg, 10 wt. %) and HCl (4 M) (3 mL). The reaction mixture was hydrogenated for 48 h at room temperature under 1 atmosphere of hydrogen. The solids were removed via filtration. The filtrate was evaporated under reduced pressure and diluted with 50 mL of water. The pH of the solution was adjusted to 7 with NaOH (2 M). The aqueous phase was extracted with 5×20 mL of ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 230 mg (51%) of the title compound as a light yellow oil.

Workup

  1. customThe solids were removed via filtration
  2. customThe filtrate was evaporated under reduced pressure
  3. additiondiluted with 50 mL of water
  4. extractionThe aqueous phase was extracted with 5×20 mL of ethyl acetate
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3d942ed28104ae5a1054b6576f44768
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…