2-(3-Bromo-4-(trifluoromethyl)phenyl)-6-ethoxyimidazo[1,2-b]pyridazine → 5-(6-Ethoxyimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)benzonitrile

HRID 539766Notes

Reaction equation

HRID 539766 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]3[N:19]([CH:20]=2)[N:18]=[C:17]([O:21][CH2:22][CH3:23])[CH:16]=[CH:15]3)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[C:24]([Cu])#[N:25]>CN1CCOCC1.CO>[CH2:22]([O:21][C:17]1[CH:16]=[CH:15][C:14]2=[N:13][C:12]([C:4]3[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[C:2]([CH:3]=3)[C:24]#[N:25])=[CH:20][N:19]2[N:18]=1)[CH3:23]

Participants

5

Reactant 2

HCID 575162022-(3-Bromo-4-(trifluoromethyl)phenyl)-6-ethoxyimidazo[1,2-b]pyridazineHCID 178418546HCID 178418546, compound

Product 1

HCID 679824015-(6-Ethoxyimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)benzonitrileYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 79724-MethylmorpholineSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 2-[3-bromo-4-(trifluoromethyl)phenyl]-6-ethoxy-imidazo[2,1-f]pyridazine (0.050 g, 0.129 mmol) and CuCN (0.058 g) in 4-methylmorpholine (2.0 mL) is heated in the microwave at 220° C. for 10 min. The mixture is diluted with MeOH (10 mL) and the solids are removed by filtration. The crude solution is concentrated to remove the MeOH. Water (50 mL) is added and the solid precipitate is collected. The crude product is purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (0.03 g, 71% yield). LCMS m/z=333.3 [M+H]+.

Workup

  1. customthe solids are removed by filtration
  2. concentrationThe crude solution is concentrated
  3. customto remove the MeOH
  4. additionWater (50 mL) is added
  5. customthe solid precipitate is collected
  6. customThe crude product is purified by silica gel chromatography (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-51fba795de2c48adb0dc1048a00f8d98
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

Loading…