6-Amino-3-chloropyridazine → 6-Chloro-2-(4-ethyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

HRID 539811Notes

Reaction equation

HRID 539811 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=1)=O>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=3)[N:8]=2)[N:7]=1

Participants

5

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 575162802-Bromo-1-(4-ethyl-3-nitrophenyl)ethanone

Product 1

HCID 575162286-Chloro-2-(4-ethyl-3-nitrophenyl)imidazo[1,2-b]pyridazineYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloropyridazin-3-amine (4.76 g, 0.037 mol) and 2-bromo-1-(4-ethyl-3-nitrophenyl)ethanone (10.0 g, 0.037 mol) in acetonitrile (100 mL) is heated at reflux for 18 hr. The reaction mixture is diluted with water (500 mL), stirred at room temperature for 1 hour and solids are collected by filtration to give the title compound (6.9 g, 62% yield). LCMS m/z=303.3, 305.4 [M+H]+, tR=2.90 min.

Workup

  1. temperatureat reflux for 18 hr
  2. filtrationsolids are collected by filtration

Sources & evidence

ORD record
ord-c41cc3cb6f3a45d498ce7fc8d3cc4d61
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

Loading…