2,6-Lutidine → 1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehyde

HRID 1959705Notes

Reaction equation

HRID 1959705 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]2[N:9]([CH2:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)[N:10]=[N:11][C:6]2=[N:5][CH:4]=1)=C.CC1C=CC=C(C)N=1.I([O-])(=O)(=O)=[O:32].[Na+]>O.O1CCOCC1.[Os](=O)(=O)(=O)=O>[N:19]1[C:20]2[C:15](=[CH:14][C:13]([CH2:12][N:9]3[C:7]4=[N:8][C:3]([CH:1]=[O:32])=[CH:4][N:5]=[C:6]4[N:11]=[N:10]3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 593418146-((6-Vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

Product 1

HCID 866520351-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehydeYield 44.7%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6-((6-vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.347 mmol) and 2,6-dimethylpyridine (74.3 mg, 0.694 mmol) was added a solution of osmium(VIII) oxide (297 mg, 1.387 mmol) in water (1.333 mL), followed by addition of a solution of sodium periodate (88 mg, 6.94 mmol) in 1,4-dioxane (4 mL). The reaction mixture was stirred at rt for 10 h. The solvent was removed in vacuo and DCM was added to dilute the residue. The resulting solution was washed with saturated NaHCO3 solution, NH4Cl and brine. The organic layer was separated, dried over Na2SO4, and concentrated to give the crude product which was purified with Analogix system on silica gel (hexanes:EtOAc) to afford 45 mg (43%) of the title compound. LCMS (method B): [MH]+=291, tR=1.00 min.

Workup

  1. customThe solvent was removed in vacuo and DCM
  2. additionwas added
  3. additionto dilute the residue
  4. washThe resulting solution was washed with saturated NaHCO3 solution, NH4Cl and brine
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified with Analogix system on silica gel (hexanes:EtOAc)

Sources & evidence

ORD record
ord-f82893ee7aeb452eaa44e395e0f04057
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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