Acrylamide → HCID 66839442, compound

HRID 546759Notes

Reaction equation

HRID 546759 reaction equation
C(N(CC)CC)C.Br[C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[CH:11][CH:10]=1.[C:23]([NH2:27])(=[O:26])[CH:24]=[CH2:25]>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:16][O:15][C:13]1[N:14]=[C:9](/[CH:25]=[CH:24]/[C:23]([NH2:27])=[O:26])[CH:10]=[CH:11][C:12]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1

Participants

7

Reactant 3

HCID 6579AcrylamideHCID 8471TriethylamineHCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

Product 1

HCID 66839442HCID 66839442, compoundYield 89.5%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (52 ml) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (49.8 g), tris(dibenzylideneacetone)dipalladium (0) (5.11 g), tri-o-tolylphosphine (3.41 g) and acrylamide (14.5 g) in N,N-dimethyl formamide (260 ml). The reaction solution was stirred at 100° C. for 50 minutes. The reaction solution was returned to room temperature and then filtered through celite. The filter cake was sequentially washed with N,N-dimethylformamide, methanol, a 50% N,N-dimethylformamide solution and N,N-dimethylformamide. The resulting filtrate was filtered through celite again, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the reaction solution was concentrated again. Toluene and a saturated sodium bicarbonate solution were added to the resulting residue, and the insoluble matter was collected by filtration. The resulting powder was dried under reduced pressure to obtain 42.96 g of the title compound. The property values of the compound are as follows.

Workup

  1. customwas returned to room temperature
  2. filtrationfiltered through celite
  3. washThe filter cake was sequentially washed with N,N-dimethylformamide, methanol
  4. filtrationThe resulting filtrate was filtered through celite again
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionToluene was added to the residue
  7. concentrationthe reaction solution was concentrated again
  8. additionToluene and a saturated sodium bicarbonate solution were added to the resulting residue
  9. filtrationthe insoluble matter was collected by filtration
  10. customThe resulting powder was dried under reduced pressure

Sources & evidence

ORD record
ord-f719a0a21da949cd89edbd2cc915c80c
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…