Acetone → HCID 69308851, compound

HRID 860447Notes

Reaction equation

HRID 860447 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:20]([CH3:22])[CH3:21])[C:9]([CH:18]=O)=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:25][C:26]([CH3:28])=[O:27]>>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:20]([CH3:22])[CH3:21])[C:9](/[CH:18]=[CH:25]/[C:26](=[O:27])[CH3:28])=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 86597470HCID 86597470, compound

Product 1

HCID 69308851HCID 69308851, compound

Procedure

To a solution of 7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazine-3-carbaldehyde (40 mg) was added 1N sodium hydroxide (19.3 mg) and acetone (0.425 mL) at ambient temperature. After 8 hours, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=5-1) to give (3E)-4-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]-pyridazin-3-yl]-3-buten-2-one as an yellow solid (33 mg).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by p-TLC (hexane-ethyl acetate=5-1)

Sources & evidence

ORD record
ord-c2007529d2fd42888acbda9d9a779cdf
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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