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

HRID 2250577Notes

Reaction equation

HRID 2250577 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-c2117d7b74c34fa2b3d73c9ca98ecd60
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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