6-Amino-3-chloropyridazine → 6-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[2,1-f]pyridazine

HRID 539746Notes

Reaction equation

HRID 539746 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]([C:19]([F:22])([F:21])[F:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1)=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2=[N:8][C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=3)=[CH:10][N:6]2[N:7]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 575162692-Bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone

Product 1

HCID 866678486-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[2,1-f]pyridazineYield 727.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 6-chloropyridazin-3-amine (0.842 g, 0.0065 mol) and 2-bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone (2.03 g, 0.65 mmol) in acetonitrile (37.34 mL) is heated at 90° C. for 48 hr. The reaction mixture is concentrated and purified by silica gel chromatography (CH2Cl2 to EtOAc) to give the title compound (1.62 g, 73% yield). LCMS m/z=343.3 [M+H]+, tR=3.15 min.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by silica gel chromatography (CH2Cl2 to EtOAc)

Sources & evidence

ORD record
ord-5f37ead536be4e8db0e0743553545e82
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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