Potassium Carbonate → 2-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylacetamide

HRID 2205909Notes

Reaction equation

HRID 2205909 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Br[CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 770224-IodopyrazoleHCID 2255442-Bromo-N,N-dimethylacetamide

Product 1

HCID 644307842-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylacetamideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-iodo-1H-pyrazole (0.95 g, 4.94 mmol) and 2-bromo-N,N-dimethylacetamide (Preparation 98, 0.82 g, 4.94 mmol) were dissolved in dry DMF (10 ml). To the stirred solution was added potassium carbonate (1 g, 7.35 mmol) and the reaction mixture was stirred for 24 hours. The solid was filtered and the solution was diluted with dichloromethane (50 ml) and water (30 ml). The organic solution was collected, dried and concentrated in vacuum. The crude was purified by silica gel column chromatography eluting with neat ethyl acetate to afford the title compound as a white crystalline solid (1.1 g, 80%). 1H-NMR (500 MHz, CDCl3): δ 3 (s, 3H), 3.09 (s, 3H), 5 (s, 2H), 7.54 (s, 1H), 7.6 (s, 1H).

Workup

  1. filtrationThe solid was filtered
  2. additionthe solution was diluted with dichloromethane (50 ml) and water (30 ml)
  3. customThe organic solution was collected
  4. customdried
  5. concentrationconcentrated in vacuum
  6. customThe crude was purified by silica gel column chromatography
  7. washeluting with neat ethyl acetate

Sources & evidence

ORD record
ord-0b2ff640d6cb4ed68bb1526a3b0b21e4
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

Loading…