Ethyl Acetate → Ethyl 6-[7-ethyl-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]hexanoate

HRID 2250582Notes

Reaction equation

HRID 2250582 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([CH:8]([C:19](=O)[CH3:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)=[CH:4][CH:3]=1.[NH2:24][N:25]1[C:29]([CH2:30][CH3:31])=[CH:28][CH:27]=[C:26]1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C(O)C.O>[CH2:30]([C:29]1[N:25]2[N:24]=[C:6]([C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=3)[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:26]2=[CH:27][CH:28]=1)[CH3:31].[CH2:32]([C:26]1[N:25]2[N:24]=[C:19]([CH3:20])[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:6]([C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=3)[C:29]2=[CH:28][CH:27]=1)[CH3:34]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 57444527Ethyl 7-(4-fluorobenzoyl)-8-oxononanoateHCID 69311541(1-amino-5-ethyl-1H-pyrrol-2-yl)(4-fluorophenyl)methanone

Product 2

HCID 69308101Ethyl 6-[7-ethyl-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]hexanoateHCID 69308766Ethyl 6-[7-ethyl-2,4-bis(4-fluorophenyl)pyrrolo[1,2-b]pyridazin-3-yl]hexanoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 7-(4-fluorobenzoyl)-8-oxononanoate (300 mg), (1-amino-5-ethyl-1H-pyrrol-2-yl)(4-fluorophenyl)methanone (216 mg), and p-toluenesulfonic acid monohydrate (35.4 mg) in ethanol (6 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 6-[7-ethyl-2,4-bis(4-fluorophenyl)pyrrolo[1,2-b]pyridazin-3-yl]hexanoate (83 mg) and ethyl 6-[7-ethyl-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]hexanoate (40 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-4f581e0d4cec4a3884a864b5e7d98ef0
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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