2-Amino-5-chloropyridine → 6-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine

HRID 539755Notes

Reaction equation

HRID 539755 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N: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:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[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)[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 575162692-Bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone

Product 1

HCID 679829716-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridineYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-amino-5-chloropyridine (0.064 g, 0.5 mmol) and 2-bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone (0.156 g, 0.5 mmol) in acetonitrile (3 ml) is stirred at 100° C. for 18 hr. The mixture is concentrated and purified on silica (0 to 100% EtOAc in hexanes) to give the title compound (165 mg, 97% yield). LCMS m/z=342.3 [M+H]+, tR=2.86 min.

Workup

  1. concentrationThe mixture is concentrated
  2. custompurified on silica (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-442119fc25624b0ca66cd25b6599288e
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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