Ethyl 4-bromobutyrate → HCID 10597233, compound

HRID 466018Notes

Reaction equation

HRID 466018 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.Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(Cl)(Cl)Cl>[CH2:30]([O:29][C:27]([CH2:26][CH2:25][CH2:24][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)=[O:28])[CH3:31]

Participants

4

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

Product 1

HCID 10597233HCID 10597233, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.47 g), ethyl 4-bromobutyrate (0.32 g), triton B (0.5 ml) and chloroform was stirred for 2 days under room temperature. The reaction mixture was evaporated and the residue was subjected to a column chromatography on silica gel (20 g) with chloroform as an eluent. The fractions containing the object compound were combined (20 ml) and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and filtered off. The filtrate was evaporated to give 3-[2-(3-ethoxycarbonylpropyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.49 g).

Workup

  1. customThe reaction mixture was evaporated
  2. additionThe fractions containing the object compound
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. filtrationfiltered off
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d26f74a61780497582dbadf8f99f24bf
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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