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

HRID 2239825Notes

Reaction equation

HRID 2239825 reaction equation
Cl.Br[C:3]1[N:4]=[C:5]2[CH:10]=[C:9]([CH3:11])[C:8]([Cl:12])=[N:7][N:6]2[CH:13]=1.[CH3:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1.CC([O-])(C)C.[K+]>C1COCC1>[Cl:12][C:8]1[C:9]([CH3:11])=[C:10]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH3:14])=[CH:22][CH:21]=2)[C:5]2[N:6]([CH:13]=[CH:3][N:4]=2)[N:7]=1

Participants

5

Reactant 3

HCID 90764-Ethoxyaniline2×HCID 23665647Potassium tert-butoxideHCID 86618518HCID 86618518, compound

Product 1

HCID 866117156-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1d variation 2) To a mixture of bromo-6-chloro-7-methylimidazo[1,2-b]pyridazine HCl salt (102 mg, 0.36 mmol) from 1c, in THF (1.5 ml) was added p-Phenetidine (49 mg, 0.36 mmol) and a 1.0 M solution of KOt-Bu in THF (3.0 eq, 1.08 ml, 1.08 mmol). The mixture was allowed to heat at 50 C for 1 hour. The solution was then concentrated in vacuo to dryness to provide 6-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amine as a solid. m/e 303 (MH+).

Workup

  1. temperatureto heat at 50 C for 1 hour
  2. concentrationThe solution was then concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-839f6f10943b41999956984bbe293e7f
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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