Sodium Iodide → HCID 11095639, compound

HRID 1363314Notes

Reaction equation

HRID 1363314 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]1.[I-].[Na+].[CH2:12](Br)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:12]([N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 11095639HCID 11095639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of NaH (125 mg, 3.12 mmol, 60% dispersion in mineral oil) in THF (10 mL), was added dropwise over 5 min, a solution of 1H-pyrazole-4-carbaldehyde (250 mg, 2.60 mmol) in THF (5 mL). The mixture was stirred at rt for 45 min; sodium iodide (10 mg) was added before the addition of phenethyl bromide (0.42 mL, 3.12 mmol). After 15 min, the reaction was heated at 80° C. for 4 h, then cooled to rt, quenched with saturated solution of NH4Cl and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (Isco CombiFlash) 0-40% EtOAc/heptane provided 1-phenethyl-1H-pyrazole-4-carbaldehyde: Yield 410 mg (79%). 1H NMR (400 MHz, CDCl3) δ ppm 3.20 (t, J=7.03 Hz, 2H), 4.39 (t, J=7.05 Hz, 2H), 7.06 (dd, J=7.91, 1.46 Hz, 2H), 7.22-7.32 (m, 3H), 7.63 (s, 1H), 8.00 (s, 1H), 9.79 (s, 1H); LCMS-MS (ESI+) 200.87 (M+H).

Workup

  1. additionwas added dropwise over 5 min
  2. waitAfter 15 min
  3. temperaturethe reaction was heated at 80° C. for 4 h
  4. temperaturecooled to rt
  5. customquenched with saturated solution of NH4Cl
  6. extractionextracted with EtOAc (3×50 mL)
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash chromatography (Isco CombiFlash) 0-40% EtOAc/heptane

Sources & evidence

ORD record
ord-e925f4aebac543c0a19794fb52896767
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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