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

HRID 860440Notes

Reaction equation

HRID 860440 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-a936da50096a4a398d4d232617be9aa1
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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