N-(4-Methoxybenzyl)aniline → 6-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

HRID 2239880

Reaction equation

HRID 2239880 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Br[C:24]1[C:25]2[N:26]([CH:31]=[CH:32][N:33]=2)[N:27]=[C:28]([Cl:30])[CH:29]=1>C1COCC1>[Cl:30][C:28]1[CH:29]=[C:24]([N:14]([CH2:13][C:12]2[CH:21]=[CH:22][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:25]2[N:26]([CH:31]=[CH:32][N:33]=2)[N:27]=1

Participants

5

Reactant 3

HCID 408377N-(4-Methoxybenzyl)anilineHCID 23665647Potassium tert-butoxideHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 596245586-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amineYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of potassium t-butoxide in THF (4.73 mL, 4.73 mmol) was added dropwise to a solution of N-(4-methoxybenzyl)aniline (0.92 g, 4.3 mmol) in THF (10 mL) at 0° C. The solution was warmed to RT for 15 minutes, recooled to 0° C. and a solution of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (1.0 g, 4.30 mmol) from Example 1, step 1b, in THF (10 mL) was added in rapidly. The solution was stirred at 0° C. for 30 minutes and then at RT for 30 minutes. The reaction solution was concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with 10% ethyl acetate/heptane to provide 0.75 g (48%) of 6-chloro-N-(4-methoxybenzyl)-N-phenyl imidazo[1,2-b]pyridazin-8-amine.

Workup

  1. customrecooled to 0° C.
  2. waitat RT for 30 minutes
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography
  5. washeluting with 10% ethyl acetate/heptane

Sources & evidence

ORD record
ord-f872ebe5ab9e4bf3836232c9d4280063
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Linked notes

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