Potassium Iodide → 1-(2,4-Dimethoxybenzyl)-4-[(4-iodo-1H-pyrazol-1-yl)methyl]-4-methylpyrrolidin-2-one

HRID 595215Notes

Reaction equation

HRID 595215 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.CS(O[CH2:12][C:13]1([CH3:30])[CH2:17][C:16](=[O:18])[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[CH2:14]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C=O)C.O>[CH3:29][O:28][C:21]1[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:20]=1[CH2:19][N:15]1[CH2:14][C:13]([CH2:30][N:4]2[CH:3]=[C:2]([I:1])[CH:6]=[N:5]2)([CH3:12])[CH2:17][C:16]1=[O:18]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 118208667[1-(2,4-Dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate

Product 1

HCID 1182084581-(2,4-Dimethoxybenzyl)-4-[(4-iodo-1H-pyrazol-1-yl)methyl]-4-methylpyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-iodo-1H-pyrazole (270 mg, 1.4 mmol), [1-(2,4-dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate (500 mg, 1.4 mmol), cesium carbonate (910 mg, 2.8 mmol), and potassium iodide (10 mg, 0.05 mmol) in DMF (80 mL) was stirred at 80° C. for 12 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give 1-(2,4-Dimethoxybenzyl)-4-[(4-iodo-1H-pyrazol-1-yl)methyl]-4-methylpyrrolidin-2-one. MS ESI calc'd. for C18H231 N3O3 [M+H]+ 456. found 456. 1H NMR (400 MHz, MeOD): δ 7.49 (s, 1H), 7.44 (s, 1H), 7.05 (d, J=8 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 6.49-6.47 (m, 1H), 4.30 (d, J=4 Hz, 2H), 4.06 (d, J=2 Hz, 2H), 3.78 (s, 6H), 3.33-3.29 (m, 1H), 2.91 (d, J=6.4 Hz, 1H), 2.54 (d, J=16.8 Hz, 1H), 2.17 (d, J=16.8 Hz, 1H), 1.01 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-2f0e9168bb694c8abcb1a8599eb89671
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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