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

HRID 539772

Reaction equation

HRID 539772 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH:10]([CH3:23])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH3:23])=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)[N:8]=2)[N:7]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 575162742-Bromo-1-(4-methyl-3-nitrophenyl)propan-1-one

Product 1

HCID 866678536-Chloro-3-methyl-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazineYield 57.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 6-chloropyridazin-3-amine (2.38 g, 18.3 mmol) and 2-bromo-1-(4-methyl-3-nitrophenyl)propan-1-one (5.0 g, 18.3 mmol) in acetonitrile (100 mL) is heated at 80° C. for 16 hours. The mixture is concentrated to dryness and then purified via silica chromatography (hexanes to EtOAc) to afford the title compound (3.2 g, 57%) as a light yellow solid: Rf 0.30 (CH2Cl2); LCMS (m/z)=303.3, 305.2 [M+H]+, tR=2.84 min.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. custompurified via silica chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-aa65a1c1e970403d875f485035c8770a
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Linked notes

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