1-Acetoxy-2-bromoethane → HCID 10496789, compound

HRID 1742283Notes

Reaction equation

HRID 1742283 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4][NH:3]1.[H-].[Na+].[C:25](OCCBr)(=[O:27])[CH3:26]>CN(C)C=O>[OH:27][CH2:25][CH2:26][N:3]1[C:2](=[O:1])[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4]1

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

Product 1

HCID 10496789HCID 10496789, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (1.0 g) and sodium hydride (60% 0.15 g) in N,N-dimethylformamide (10 ml) was added acetoxyethyl bromide (0.58 g) at 5° C., and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into ice-water, and extracted twice with ethyl acetate. The extracts were combined, washed successively with 1N sodium hydroxide solution and sodium chloride aqueous solution, dried over magnesium sulfate, and then evaporated in vacuo. The residue was dissolved in 1,4-dioxane (12 ml) and a solution of sodium hydroxide (0.34 g) in water (1.5 ml) was added thereto. The reaction mixture was stirred at 60° C. for 3 hours, and evaporated in vacuo. The residue was treated with water and extracted with chloroform. The extract was washed with sodium chloride aqueous solution, dried over magnesium sulfate, and then evaporated in vacuo. The residue was crystallized from ethyl acetate to afford 3-[ 2-(2-hydroxyethyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.84 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed successively with 1N sodium hydroxide solution and sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in 1,4-dioxane (12 ml)
  6. additiona solution of sodium hydroxide (0.34 g) in water (1.5 ml) was added
  7. stirringThe reaction mixture was stirred at 60° C. for 3 hours
  8. customevaporated in vacuo
  9. additionThe residue was treated with water
  10. extractionextracted with chloroform
  11. washThe extract was washed with sodium chloride aqueous solution
  12. dry with materialdried over magnesium sulfate
  13. customevaporated in vacuo
  14. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-60ec4a6eb9984154a17ac319e7c09bbe
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

Loading…