3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

HRID 1892318

Reaction equation

HRID 1892318 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CC[Mg+].[Br-].[F:16][C:17]1[C:26]([CH:27]=[O:28])=[C:25]([F:29])[CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([CH:27]([C:26]3[C:17]([F:16])=[C:18]4[C:23](=[CH:24][C:25]=3[F:29])[N:22]=[CH:21][CH:20]=[CH:19]4)[OH:28])=[CH:3][N:4]=2)[N:7]=1

Participants

5

Reactant 3

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 579172825,7-Difluoroquinoline-6-carbaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 58147519(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine (2.40 g, 10.35 mmol) in 30 mL of THF was added EtMgBr (1M in THF, 12.43 mL, 12.42 mmol) solution at rt. The solution was stirred for 30 min and a solution of 5,7-difluoroquinoline-6-carbaldehyde (2.0 g, 10.35 mmol) in 10 mL of THF was added. The resulting mixture was stirred at rt for additional 2 h and then quenched with 50 mL of NH4Cl solution. The solution was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to afford 3.48 g (97%) of the title compound. LCMS (method B): [MH]+=347, tR=1.23 min.

Workup

  1. stirringThe resulting mixture was stirred at rt for additional 2 h
  2. customquenched with 50 mL of NH4Cl solution
  3. extractionThe solution was extracted with EtOAc
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e51f20782c284a36bcfcb3c8c727a239
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Linked notes

Loading…