Hydrochloric Acid → HCID 86723028, compound

HRID 522316Notes

Reaction equation

HRID 522316 reaction equation
Cl.CC(OC(=O)N[C:9]1[CH:10]=[N:11][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:13]=1[I:14])(C)C>O1CCOCC1>[I:14][C:13]1[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86723029HCID 86723029, compound

Product 1

HCID 86723028HCID 86723028, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid in dioxane (4 N, 3 mL) was added to 5-iodo-1-(3-fluorophenyl)-1H-pyrazol-4-yl-carbamic acid 1,1-dimethylethyl ester (348 mg, 0.864 mmol) at ambient temperature. The reaction was stirred overnight at the same temperature. Solvent was removed under reduced pressure. The crude material was dissolved in ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude material was purified using silica gel column chromatography (20-60% ethyl acetate in hexanes) to afford 5-iodo-1-(3-fluorophenyl)-1H-pyrazol (210 mg, 0.695 mmol, 80% yield).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionThe crude material was dissolved in ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice more with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. customAfter removal of the solvent under reduced pressure
  7. customthe crude material was purified

Sources & evidence

ORD record
ord-7d3b4f5732d34f77b7f871260e47b8e9
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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