Triacetoxyperiodinane → Imidazo[1,2-b]pyridazine-3-carbaldehyde

HRID 869478Notes

Reaction equation

HRID 869478 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:10][OH:11])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[N:1]1[CH:2]=[C:3]([CH:10]=[O:11])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71744071HCID 71744071, compound

Product 1

HCID 45083595Imidazo[1,2-b]pyridazine-3-carbaldehydeYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of imidazo[1,2-b]pyridazin-3-ylmethanol (45 mg, 0.3 mmol) and Dess-Martin periodinane (130 mg, 0.3 mmol) in anhydrous DCM (5 mL) were stirred at RT overnight. The reaction mixture was quenched with water (5 mL). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to afford imidazo[1,2-b]pyridazine-3-carbaldehyde (40 mg, 90.7% yield).

Workup

  1. customThe reaction mixture was quenched with water (5 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4cf7c16a8cc64a238b23a4b4c272371b
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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