tert-Butanol → HCID 57917443, compound

HRID 69145

Reaction equation

HRID 69145 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 57917443HCID 57917443, compound

Reagents, catalysts & solvents 3

HCID 23937OsmiumCatalystHCID 516892Sodium BicarbonateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0cef86927abf407b9d0afff550992f00
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

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