Water → HCID 19009005, compound

HRID 1590626Notes

Reaction equation

HRID 1590626 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[O:8]=[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)=[N:11][NH:10]1.[H-].[Na+].O>CN(C)C=O.[I-].[K+]>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:10]1[C:9](=[O:8])[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)=[N:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

Product 1

HCID 19009005HCID 19009005, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Potassium iodide (0.1 g) and 1,5-dibromopentane (4.6 g) were added to a suspension of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.88 g) and 60% sodium hydride [0.4 g) in N,N-dimethylformamide (40 ml). After being stirred for 3 hours at room temperature, the mixture was poured into cold water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (100 g) using chloroform as an eluent to afford 3-[2-(5-bromopentyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (3.48 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe oily residue was purified by column chromatography on silica gel (100 g)

Sources & evidence

ORD record
ord-baa346ef539247c5a8c3101d234add81
Source dataset
uspto-grants-1993_04
Patent number
US05204346

Reaction notes

Loading…