Acetyl chloride → 4-(3-acetyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

HRID 2426517Notes

Reaction equation

HRID 2426517 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].ClCCCl.[Cl-].[Al+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.C[O:21][C:22]1[N:23]=[N:24][C:25]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[CH:26][C:27]=1[C:28]1[NH:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2>>[C:1]([C:36]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][C:28]=1[C:27]1[C:22](=[O:21])[NH:23][N:24]=[C:25]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[CH:26]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 230924532-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole trifluoroacetateHCID 86612051Aluminium chloride 1,2-dichloroethane

Product 1

HCID 1354894934-(3-acetyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-oneYield 48.1%

Conditions

Temperature
50 °C

Procedure

4 mg acetyl chloride are added at 0° C. to a suspension of 80 mg aluminum chloride 1,2-Dichloroethane, followed by 208 mg 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole Trifluoroacetate. The reaction mixture is stirred for 4 h at room temperature and for 3 h at 50° C. It is worked up pouring into an ice/water mixture and filtering. The layers are separated, the organic layer is washed with water, dried over MgSO4 and the solvent removed. Reverse phase HPLC chromatography yielded 8.1 mg 4-(3-Acetyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one.

Workup

  1. filtrationfiltering
  2. customThe layers are separated
  3. washthe organic layer is washed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent removed

Sources & evidence

ORD record
ord-49983c1fdbd34da5bc78ea4982318048
Source dataset
uspto-grants-2011_06
Patent number
US07968546B2

Reaction notes

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