Selenium Dioxide → 6-(1-Formylisoquinolin-4-yloxy)nicotinamide

HRID 2060858Notes

Reaction equation

HRID 2060858 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1.[Se](=O)=[O:23]>O1CCOCC1>[CH:1]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1)=[O:23]

Participants

4

Reactant 2

HCID 24007Selenium Dioxide2×HCID 594013386-(1-Methylisoquinolin-4-yloxy)nicotinamide

Product 1

HCID 594013146-(1-Formylisoquinolin-4-yloxy)nicotinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To 6-(1-methylisoquinolin-4-yloxy)nicotinamide (Preparation 19) (135 mg, 0.48 mmol) in dioxane (6 mL) under argon was added selenium dioxide (54 mg, 0.48 mmol). The mixture was heated to 80° C. for 3 h after which time selenium dioxide (54 mg, 0.48 mmol) was added. After a further 0.5 h at 80° C. the mixture was cooled, filtered through Celite and washed with EtOAc (50 mL). The organic phase was washed with NaHCO3 (30 mL), water (30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=2.93 min; m/z (ES+)=294.1 [M+H]+.

Workup

  1. additionwas added
  2. filtrationfiltered through Celite
  3. washwashed with EtOAc (50 mL)
  4. washThe organic phase was washed with NaHCO3 (30 mL), water (30 mL), brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-1a9721ef29524af5b71524a288fd620d
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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