Diiodomethane → HCID 86723026, compound

HRID 522314Notes

Reaction equation

HRID 522314 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[I:19]CI.N(OCCC(C)C)=O>C(#N)C>[I:19][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 45494362Ethyl 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 86723026HCID 86723026, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate (518 mg, 2.08 mmol) was suspended in acetonitrile (5 mL) at ambient temperature. Diiodomethane (675 μL, 8.38 mmol) was added followed by isopentyl nitrite (565 μL, 4.21 mmol). The reaction was heated at 50° C. for one hour and was then partitioned between water and ethyl acetate. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate. After removal of solvents under reduced pressure, the crude material was purified using silica gel column chromatography (10-25% ethyl acetate in hexanes) to afford ethyl 5-iodo-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate (589 mg, 1.64 mmol, 79% yield).

Workup

  1. customwas then partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted twice more with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customAfter removal of solvents under reduced pressure
  5. customthe crude material was purified

Sources & evidence

ORD record
ord-bf3d2f1d09524be2b54e77bc4fa61c05
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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