Propargyl bromide → HCID 86741554, compound

HRID 651989Notes

Reaction equation

HRID 651989 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:19]=[C:13]2[C:14](=[O:18])[NH:15][CH2:16][CH:17]=[C:12]2[N:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]#[CH:28]>S1(CCCC1)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:28][C:27]#[CH:26])[CH:6]=[CH:5][C:4]=1[C:10]1[N:19]=[C:13]2[C:14](=[O:18])[NH:15][CH2:16][CH:17]=[C:12]2[N:11]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 1363936692-(2-methoxy-4-hydroxy-phenyl)-5H-imidazo[4,5-c]pyridin-4-one

Product 1

HCID 86741554HCID 86741554, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

1 g of 2-(2-methoxy-4-hydroxy-phenyl)-5H-imidazo[4,5-c]pyridin-4-one was suspended in 30 ml of sulfolane, 1.41 g of potassium carbonate were added, and the mixture was stirred at room temperature. After 15 minutes and again after one hour, 0.9 ml of propargyl bromide was added, and the mixture was then stirred for another 1.25 hours. The solvent was substantially evaporated in vacuo, and the residue was stirred with methylene chloride. After the precipitate had been filtered off and washed with water, the product contained in the organic phase was purified on a silica gel column (eluant: methylene chloride/ethanol 1:0 to 1:0.03). The product crystallized with half a mol of ethanol.

Workup

  1. waitagain after one hour
  2. stirringthe mixture was then stirred for another 1.25 hours
  3. customThe solvent was substantially evaporated in vacuo
  4. stirringthe residue was stirred with methylene chloride
  5. filtrationAfter the precipitate had been filtered off
  6. washwashed with water
  7. customwas purified on a silica gel column (eluant: methylene chloride/ethanol 1:0 to 1:0.03)
  8. customThe product crystallized with half a mol of ethanol

Sources & evidence

ORD record
ord-8e2aed4655304348bfc9f9cea1188899
Source dataset
uspto-grants-1987_06
Patent number
US04670438

Reaction notes

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