2,6-Lutidine → 5,7-Difluoroquinoline-6-carbaldehyde

HRID 1942054Notes

Reaction equation

HRID 1942054 reaction equation
[F:1][C:2]1[C:11]([CH:12]=C)=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:24].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:11]([CH:12]=[O:24])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 579173805,7-Difluoro-6-vinyl-quinoline

Product 1

HCID 579172825,7-Difluoroquinoline-6-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

5,7-Difluoro-6-vinyl-quinoline ((vii), 614 mg, 3.21 mmol) was dissolved in dioxane (1.7 mL) and water (0.6 mL). 2,6-lutidine (0.761 mL, 6.42 mmol), sodium periodate (2.75 g, 12.85 mmol) and osmium tetroxide (653 mg, 0.064 mmol) were added to the previous solution. The RM was stirred at RT for 15 min. A precipitate was formed. Water was added to the RM and it was extracted twice with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by MPLC with Hexane and EtOAc to give the title compound as a white solid (tR 1.2 min (conditions 4), MH+=244, 1H-NMR in DMSO-d6: 10.36 (s, 1H); 9.15 (s, 1H); 8.65 (d, 1H); 7.79 (d, 1H); 7.69 (dd, 1H)).

Workup

  1. customA precipitate was formed
  2. extractionwas extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed
  6. customThe residue was purified by MPLC with Hexane and EtOAc

Sources & evidence

ORD record
ord-19f40f7a7dc34fc6af6bc8b61026c41a
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

Loading…