N-(4-Methoxybenzyl)aniline → HCID 86611750, compound

HRID 2239869

Reaction equation

HRID 2239869 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[Br:23][C:24]1[N:28]2[N:29]=[C:30]([Cl:34])[CH:31]=[C:32](Br)[C:27]2=[N:26][CH:25]=1>CN(C=O)C.C(OCC)(=O)C>[Br:23][C:24]1[N:28]2[N:29]=[C:30]([Cl:34])[CH:31]=[C:32]([N:8]([CH2:7][C:6]3[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:27]2=[N:26][CH:25]=1

Participants

6

Reactant 3

HCID 408377N-(4-Methoxybenzyl)anilineHCID 23665647Potassium tert-butoxideHCID 446307233,8-Dibromo-6-chloroimidazo[1,2-b]pyridazine

Product 1

HCID 86611750HCID 86611750, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-(4-Methoxybenzyl)aniline (215 mg, 1 mmol) was dissolved in dry DMF (4 mL), placed under a nitrogen atmosphere, and cooled to 0° C. in an ice bath. Potassium t-butoxide (1 mL, 1 mmol, 1M THF solution) was added and the mixture was allowed to stir for 10 min at 0° C. and room temperature for 30 min. The resulting mixture was cool to 0° C. Solid 3,8-dibromo-6-chloroimidazo[1,2-b]pyridazine (310 mg, 1 mmol) from Example XXIV, step 1a was added. The mixture was allowed to stir for 30 min at 0° C. and overnight at room temperature. The mixture was diluted with ethyl acetate (100 mL), washed sequentially with 10% LiCl, water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and the resulting material was purified by silica gel chromatography (ethyl acetate/heptane, 25 min gradient: 5-50% ethyl acetate) to provide 0.27 g of 3-bromo-6-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine.

Workup

  1. temperatureThe resulting mixture was cool to 0° C
  2. stirringto stir for 30 min at 0° C. and overnight at room temperature
  3. washwashed sequentially with 10% LiCl, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe resulting material was purified by silica gel chromatography (ethyl acetate/heptane, 25 min gradient: 5-50% ethyl acetate)

Sources & evidence

ORD record
ord-c22ae23dea044d9cb5fc562d0492be7c
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Linked notes

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