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1-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-one → 1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol

HRID 456145
Notes
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Reaction equation

HRID 456145 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([CH3:12])[N:6]=[CH:5]2.[Li]CCCC.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([C:28](=[O:30])[CH3:29])=[CH:26][N:27]=2)[N:24]=1>C1COCC1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][C:10]=3[F:11])[N:7]([CH3:12])[N:6]=[CH:5]4)([OH:30])[CH3:29])=[CH:26][N:27]=2)[N:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 132488051-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-oneHCID 579172745-Bromo-6-fluoro-1-methyl-1H-indazoleHCID 178418339Butyllithium

Product 1

HCID 581475401-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanolYield 34%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
-100 °C

Procedure

To a solution of 5-bromo-6-fluoro-1-methyl-1H-indazole (1.800 g, 7.86 mmol) in THF (79 ml) at −100° C., was added n-BuLi (5.40 ml, 8.64 mmol) dropwise. After stirring for 1 h at −100° C., 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone (1.691 g, 8.64 mmol) in THF (20 mL) was added dropwise. The reaction solution was stirred for additional 2 h and was quenched with NH4Cl (aq). The resulting mixture was extracted with EtOAc. Combined organic layers were washed with NH4Cl(aq), dried over Na2SO4 and concentrated in vacuo to afford a crude product, which was purified on silica gel column chromatography (Hexanes:EtOAc) to give the title compound in 34% yield. LCMS (method B): [MH]+=346, tR=2.14 min.

Workup

  1. stirringThe reaction solution was stirred for additional 2 h
  2. customwas quenched with NH4Cl (aq)
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washCombined organic layers were washed with NH4Cl(aq)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford a crude product, which
  8. customwas purified on silica gel column chromatography (Hexanes:EtOAc)

Sources & evidence

ORD record
ord-86aa3fd74ed7416080297d0885bf276e
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497368B2

Reaction notes

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