Cesium carbonate → HCID 70926705, compound

HRID 240487Notes

Reaction equation

HRID 240487 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[CH2:9]([N:11]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[O:18])[NH:12]1)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[CH2:9]([N:11]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[O:18])[N:12]1[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1)[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27831792-Fluoro-5-iodopyridineHCID 12240358HCID 12240358, compound

Product 1

HCID 70926705HCID 70926705, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(200 mg, 0.90 mmol) 2-Fluoro-5-iodopyridine was dissolved in toluene (1 ml) and 1-ethyl-5,5-dimethyl-pyrazolidin-3-one [CAS 26485-97-2] (128 mg, 0.90 mmol, 1.0 equiv.) and cesium carbonate (440 mg, 1.35 mmol, 1.5 equiv.) were added under nitrogen. The mixture was stirred for 4 hours at 100° C. The crude product was purified by flash chromatography by directly loading the toluene mixture onto a silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 50:50. The desired 1-ethyl-2-(5-iodo-pyridin-2-yl)-5,5-dimethyl-pyrazolidin-3-one (88 mg, 28% yield) was obtained as a yellow oil, MS: m/e=346.3 (M+H+).

Workup

  1. customThe crude product was purified by flash chromatography
  2. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-5f8b2743423d425cb4236f558e379188
Source dataset
uspto-grants-2014_02
Patent number
US08648088B2

Reaction notes

Loading…