Chloroacetaldehyde → 8-Bromo-6-chloro-7-phenylimidazo[1,2-b]pyridazine hydrochloride

HRID 2239840Notes

Reaction equation

HRID 2239840 reaction equation
[Cl:1][CH2:2][CH:3]=O.[Br:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[N:9]=[N:8][C:7]=1[NH2:19]>CCO>[ClH:1].[Br:5][C:6]1[C:7]2[N:8]([CH:2]=[CH:3][N:19]=2)[N:9]=[C:10]([Cl:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 866117234-Bromo-6-chloro-5-phenylpyridazin-3-amine

Product 1

HCID 866117218-Bromo-6-chloro-7-phenylimidazo[1,2-b]pyridazine hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
118 °C

Procedure

Chloroacetaldehyde (2.0 mL, 31.5 mmol) was added to a solution of crude 4-bromo-6-chloro-5-phenylpyridazin-3-amine (0.193 g, 0.676 mmol) from 1b in EtOH (5.0 mL). The mixture was heated in a sealed tube at 118° C. for 5 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo, and suspended in acetone/Et2O (1:1, 3 mL), filtered, and washed with Et2O to give 8-bromo-6-chloro-7-phenylimidazo[1,2-b]pyridazine HCl salt (0.147 g, >94% purity).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. filtrationfiltered
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-8794c8292d6f44f4b95ebc0f4ac8f72e
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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