tert-Butanol → HCID 57917443, Verbindung

HRID 69145

Reaktionsgleichung

Reaktionsgleichung von HRID 69145
[F:1][C:2]1[C:7]([CH:8]=C)=[CH:6][N:5]2[CH:10]=[CH:11][N:12]=[C:4]2[CH:3]=1.I([O-])(=O)(=O)=[O:14].[Na+].N1C(C)=CC=CC=1C.C(O)(C)(C)C>O1CCOCC1.O.C([O-])(O)=O.[Na+].[Os]>[F:1][C:2]1[C:7]([CH:8]=[O:14])=[CH:6][N:5]2[CH:10]=[CH:11][N:12]=[C:4]2[CH:3]=1

Komponenten

8

Edukt 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 57917482HCID 57917482, Verbindung

Produkt 1

HCID 57917443HCID 57917443, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23937OsmiumKatalysatorHCID 516892Sodium BicarbonateLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 7-fluoro-6-vinyl-imidazo[1,2-a]pyridine (xv) (94 mg, 0.58 mmol), sodium periodate (496 mg, 2.32 mmol) and 2,6-lutidine (0.135 mL, 1.16 mmol) in dioxane/water 3:1 (4.8 mL) was added in two portions a 2.5% solution of osmium tetroxyde in tert-butanol (2×0.728 mL, 2×0.058 mmol). The RM was stirred at rt for 19.5 h and at 50° C. for 24 h. The RM was diluted with aqueous saturated NaHCO3 and extracted twice with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by chromatography with DCM and MeOH to yield the title product as a brown solid (TLC RF (DCM/MeOH 9: 1)=0.40, MH+=165).

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography with DCM and MeOH

Quellen und Nachweise

ORD-Eintrag
ord-0cef86927abf407b9d0afff550992f00
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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