Sodium Iodide → N-(1-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)pyrrolidin-3-yl)acetamide

HRID 220002Notes

Reaction equation

HRID 220002 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:9]=[C:8]([CH3:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[N:6]=1.[NH:19]1[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:27])[CH3:26])[CH2:20]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C)C=O>[Cl:18][C:13]1[CH:12]=[C:11]([N:7]2[C:8]([CH3:10])=[CH:9][C:5]([O:4][CH2:3][CH2:2][N:19]3[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:27])[CH3:26])[CH2:20]3)=[N:6]2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 5227153-AcetamidopyrrolidineHCID 250231333-(2-chloroethoxy)-1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazole

Product 1

HCID 57919736N-(1-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)pyrrolidin-3-yl)acetamideYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-chloroethoxy)-1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazole (0.5 g, 1.64 mmol), N-(pyrrolidin-3-yl)acetamide (0.23 g, 1.8 mmol), K2CO3 (0.68 g, 4.9 mmol) and NaI (245 mg, 1.64 mmol) in dry dimethylformamide (10 ml) was warmed overnight at 85° C., and then an additionally 16 hrs at 95° C., in a dry nitrogen atmosphere. Solvents were evaporated in vacuo and the crude residue partitioned in water/ethyl acetate. The combined organic extracts were washed with water, dried on Na2SO4 and concentrated in vacuo to obtain a yellow crude oil, which was purified by column chromatography on silica gel (eluent: ethyl acetate 100% and ethyl acetate/MeOH 9/1) yielding 192 mg of N-(1-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)pyrrolidin-3-yl)acetamide as an oil.

Workup

  1. customan additionally 16 hrs
  2. customat 95° C.
  3. customSolvents were evaporated in vacuo
  4. customthe crude residue partitioned in water/ethyl acetate
  5. washThe combined organic extracts were washed with water
  6. customdried on Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto obtain a yellow crude oil, which
  9. customwas purified by column chromatography on silica gel (eluent: ethyl acetate 100% and ethyl acetate/MeOH 9/1)

Sources & evidence

ORD record
ord-6172262d421642129298465eb048ccfc
Source dataset
uspto-grants-2012_06
Patent number
US08202872B2

Reaction notes

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