Water → Ethyl 2-benzyl-4-(4-fluorophenyl)pyrrolo[1,2-b]pyridazine-3-carboxylate

HRID 860433Notes

Reaction equation

HRID 860433 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([CH:8]([C:14](=O)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O)=[CH:4][CH:3]=1.[N:25]1([NH2:30])[CH:29]=[CH:28][CH:27]=[CH:26]1.C(OCC)(=O)C.O>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:15]([C:14]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:5]2[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=2)[C:26]2[N:25]([CH:29]=[CH:28][CH:27]=2)[N:30]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 1365891-AminopyrroleHCID 57444525Ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate

Product 1

HCID 69308257Ethyl 2-benzyl-4-(4-fluorophenyl)pyrrolo[1,2-b]pyridazine-3-carboxylateYield 51.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate (1.4 g), 1H-pyrrol-1-amine (350 mg), and p-toluenesulfonic acid monohydrate (41 mg) in ethanol (10 ml) was refluxed for 5 hours. The mixture was partioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 2-benzyl-4-(4-fluorophenyl)pyrrolo[1,2-b]pyridazine-3-carboxylate (828 mg) as an oil.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4)

Sources & evidence

ORD record
ord-37b289889c444eefa9b6c3a85e721145
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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