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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 1892368
Notes
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Reaction equation

HRID 1892368 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-one2×HCID 579172745-Bromo-6-fluoro-1-methyl-1H-indazole2×HCID 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 (intermediate L) (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., a solution of 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone (intermediate M) (1.691 g, 8.64 mmol) in THF (20 mL) was added dropwise. The reaction solution was stirred for additional 2 h and quenched with NH4Cl (aq). The resulting mixture was extracted with EtOAc. The combined organic layers were washed with NH4Cl (aq), dried over Na2SO4 and concentrated in vacuo to afford the crude product which was purified by 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. customquenched with NH4Cl (aq)
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washThe combined organic layers were washed with NH4Cl (aq)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product which
  8. customwas purified by column chromatography (hexanes:EtOAc)

Sources & evidence

ORD record
ord-0e19a0c69b174457bb7d1232b341f144
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507676B2

Reaction notes

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