4-Ethoxyaniline → 6-chloro-N-(4-ethoxyphenyl)-7-phenylimidazo[1,2-b]pyridazin-8-amine

HRID 2239841Notes

Reaction equation

HRID 2239841 reaction equation
Cl.Br[C:3]1[C:4]2[N:5]([CH:16]=[CH:17][N:18]=2)[N:6]=[C:7]([Cl:15])[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=1.CC([O-])(C)C.[K+]>>[Cl:15][C:7]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:3]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH3:19])=[CH:27][CH:26]=2)[C:4]2[N:5]([CH:16]=[CH:17][N:18]=2)[N:6]=1

Participants

4

Reactant 3

HCID 90764-Ethoxyaniline2×HCID 23665647Potassium tert-butoxideHCID 866117218-Bromo-6-chloro-7-phenylimidazo[1,2-b]pyridazine hydrochloride

Product 1

HCID 866117246-chloro-N-(4-ethoxyphenyl)-7-phenylimidazo[1,2-b]pyridazin-8-amine

Procedure

To a solution of 8-bromo-6-chloro-7-phenylimidazo[1,2-b]pyridazine HCl salt (0.0431 g, 0.125 mmol) from 1c and 4-ethoxyaniline (0.31 M in THF, 0.40 mL) under nitrogen at 0° C. was added KOtBu (1 N in THF, 0.32 mL, 0.32 mmol). After 1 min, the cold bath was removed, and the reaction mixture was stirred to room temperature for 1 h. After concentrating in vacuo, the residue was taken up in CH2Cl2 and water, and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo. Trituration with hexanes provided 6-chloro-N-(4-ethoxyphenyl)-7-phenylimidazo[1,2-b]pyridazin-8-amine (0.0334 g).

Workup

  1. customthe cold bath was removed
  2. concentrationAfter concentrating in vacuo
  3. customwater, and the layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd882a8bb68a4e0d90ec3e418f74046e
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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