N-Iodosuccinimide → 6-chloro-3-iodo-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

HRID 2239891Notes

Reaction equation

HRID 2239891 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C1C(=O)N([I:34])C(=O)C1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:11]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[N:6]([C:8]([I:34])=[CH:9][N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 596245586-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

Product 1

HCID 866185226-chloro-3-iodo-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 6-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (940 mg, 2.57 mmol) from Example X, step (1a) in chloroform (10 mL) at room temperature was added NIS in one portion and the resulting mixture was refluxed for 5 h. Concentration and purification by flash chromatography provided 6-chloro-3-iodo-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine as a foamy, yellow solid (960 mg, 76%). LCMS [M+H]+ 490.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 h
  2. concentrationConcentration and purification by flash chromatography

Sources & evidence

ORD record
ord-09b9335a08a845b88dcf68e41057e748
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

Loading…