{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate → HCID 57423120, compound

HRID 15328Notes

Reaction equation

HRID 15328 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([OH:18])=[CH:8][N:7]=1)(=[O:3])[CH3:2]>N1C=CC=CC=1.[Cu]I>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]2[CH:12]=[C:13]([Si:14]([CH3:16])([CH3:15])[CH3:17])[O:18][C:9]2=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 57423119{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

Product 1

HCID 57423120HCID 57423120, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Procedure

{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate (8.3 g, 22 mmol) was dissolved in pyridine (200 ml) and treated with copper(I) iodide (5.2 g, 27 mmol) then heated under reflux for 18 h. The mixture was allowed to cool then evaporated to dryness. The residue was partitioned between water and ethyl acetate then filtered through kieselguhr. The organic layer was separated washed with more water then saturated brine solution then dried. Chromatography on silica gel eluting with 40-60 petrol and ethyl acetate gradient provided the two title compounds, (1.15 g, 27%) of furo[2,3-c]pyridin-5-ylmethyl acetate and (1.3 g, 22%) of [2-(trimethylsilyl)furo[2,3-c]pyridin-5-yl]methyl acetate.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 18 h
  3. temperatureto cool
  4. customthen evaporated to dryness
  5. customThe residue was partitioned between water and ethyl acetate
  6. filtrationthen filtered through kieselguhr
  7. customThe organic layer was separated
  8. washwashed with more water
  9. dry with materialsaturated brine solution then dried

Sources & evidence

ORD record
ord-1ef24485664b41448ac750d5ab769323
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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