Methyl morpholine oxide → 1-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone

HRID 2193032Notes

Reaction equation

HRID 2193032 reaction equation
[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16](C)=[CH2:17])=[N:11]2)[CH2:2][CH2:3][CH3:4].C[N+]1([O-])CC[O:28]CC1>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16](=[O:28])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 59375395HCID 59375395, compound

Product 1

HCID 593755411-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine (100 mg, 0.320 mmol) in tetrahydrofuran (1.0 ml) and water (0.25 ml) was added 4-methylmorpholine 4-oxide (NMO) (39.6 mg, 0.338 mmol) followed by osmium tetroxide (525 uL of a 4 wt % aqueous solution. The reaction mixture was stirred at room temperature for 1 hr. Additional tetrahydrofuran (1.0 ml) and water (0.25 ml) were added, followed by an additional portion of NMO (39.6 mg, 0.338 mmol). The reaction mixture was partitioned between EtOAc and water. The organic layer was dried over sodium sulfate, filtered, and concentrated to a crude residue that was adsorbed on to silica gel and purified by silica gel chromatography eluting with an EtOAc/hexanes gradient to afford 1-(1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone. LRMS (ESI) calc'd for (C18H17FN2O2) [M+H]+, 313.1; found 313.1.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a crude residue that
  5. custompurified by silica gel chromatography
  6. washeluting with an EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-1e4195eca2614cf49a032c5f7d7f13b6
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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