Methyl morpholine oxide → HCID 58081550, compound

HRID 341204Notes

Reaction equation

HRID 341204 reaction equation
[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:5]2=[N:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58081505IMidazo[1,2-a]pyridine-7-Methanol, 3-iodo-

Product 1

HCID 58081550HCID 58081550, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-Iodo-imidazo[1,2-a]pyridin-7-yl)methanol (1.00 g, 3.65 mmol) and NMO (0.64 g, 5.47 mmol) in CH2Cl2 (30 ml) with sieves (3 g) at 0° C. was added TPAP (0.06 g, 0.18 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 h, before being filtered to remove the sieves. The organic layer was washed with H2O (×2), dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by silica column chromatography (0-60% MeOH in Et2O) to afford the product (0.15 g). MS: [M+H]+=273

Workup

  1. filtrationbefore being filtered
  2. customto remove the sieves
  3. washThe organic layer was washed with H2O (×2)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by silica column chromatography (0-60% MeOH in Et2O)

Sources & evidence

ORD record
ord-58abc2f48ed84de8b6b3c85f100c6637
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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