Triacetoxyperiodinane → 3-Bromo-8-morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde

HRID 718582Notes

Reaction equation

HRID 718582 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH2:17][OH:18].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH:17]=[O:18]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117728706(3-Bromo-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

Product 1

HCID 1177288343-Bromo-8-morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 14a (3.1 g, 9.9 mmol) in DCM (200 mL) was added Dess-Martin periodinane (4.6 g, 11 mmol). The reaction mixture was stirred at rt for 16 h, diluted with DCM (100 mL), and washed with 10% Na2S2O3 solution (50 mL) and aq Na2CO3 solution (2M, 100 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give a residue, which was washed with MeOH (2×20 mL) and Et2O (2×20 mL) to afford compound 14b as an off-white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.13 (s, 1H), 8.19 (d, J=5.56 Hz, 1H), 6.15 (d, J=5.56 Hz, 1H), 4.01-4.10 (m, 4H), 3.86-3.97 (m, 4H).

Workup

  1. washwashed with 10% Na2S2O3 solution (50 mL) and aq Na2CO3 solution (2M, 100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. washwas washed with MeOH (2×20 mL) and Et2O (2×20 mL)

Sources & evidence

ORD record
ord-80e760c165d04d7b9f03292c2ad37db3
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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