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

HRID 1959705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959705
[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

Komponenten

7

Edukt 3

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

Produkt 1

HCID 866520351-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehydeAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f82893ee7aeb452eaa44e395e0f04057
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410264B2

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