Triacetoxyperiodinane → 1-(3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-one

HRID 456178Notes

Reaction equation

HRID 456178 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]1[N:17]2[N:18]=[C:19]([CH:22]([OH:25])[CH2:23][CH3:24])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]1[N:17]2[N:18]=[C:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 669271811-(3-((6-Fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-ol

Product 1

HCID 669272741-(3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 1-(3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-ol (13 mg, 0.015 mmol) in DCM (3 mL), was added TEA (0.011 ml, 0.079 mmol) and Dess-Martin periodinane (40 mg, 0.094 mmol). After stirring at rt for 10 min, the reaction was quenched with Na2SO3(aq), extracted with DCM. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with gradient Hex:EA to give 1-(3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-one (4 mg, 74%). LCMS (method A): [MH]+=338, tR=5.08 min.

Workup

  1. customthe reaction was quenched with Na2SO3(aq)
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue, which
  7. customwas purified by silica gel column chromatography with gradient Hex

Sources & evidence

ORD record
ord-ce1baf28cf154a6eb09be257a9bd21f3
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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