Water → Ethyl[4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetate

HRID 860435Notes

Reaction equation

HRID 860435 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([CH:8]([C:15](=O)[CH3:16])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[CH:4][CH:3]=1.[N:20]1([NH2:25])[CH:24]=[CH:23][CH:22]=[CH:21]1.C(OCC)(=O)C.O>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][C:8]1[C:15]([CH3:16])=[N:25][N:20]2[CH:24]=[CH:23][CH:22]=[C:21]2[C:6]=1[C:5]1[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 1365891-AminopyrroleHCID 57444526Ethyl 3-(4-fluorobenzoyl)-4-oxopentanoate

Product 1

HCID 91147555Ethyl[4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetateYield 116.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(4-fluorobenzoyl)-4-oxopentanoate (800 mg), 1H-pyrrol-1-amine (265 mg), and p-toluenesulfonic acid monohydrate (31 mg) in ethanol (5 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[4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetate (1.09 g) 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-d42400a0d0144e6bb03352aa4b1cf16a
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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