Potassium Phosphate, Tribasic → 4-iodo-2H,3H-furo(2,3-b)pyridine

HRID 1499422Notes

Reaction equation

HRID 1499422 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].F[C:10]1[C:15]([CH2:16][CH2:17][OH:18])=[C:14]([I:19])[CH:13]=[CH:12][N:11]=1>O1CCOCC1>[I:19][C:14]1[CH:13]=[CH:12][N:11]=[C:10]2[O:18][CH2:17][CH2:16][C:15]=12

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 684325752-(2-Fluoro-4-iodopyridin-3-yl)ethan-1-ol

Product 1

HCID 867266744-iodo-2H,3H-furo(2,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Potassium phosphate (10.0 g, 47.1 mmol) was added to a solution of 2-(2-fluoro-4-iodopyridin-3-yl)ethanol (3.13 g, 11.7 mmol) in 1,4-dioxane (100 mL). The mixture was heated under reflux for 36 h. The reaction mixture was filtered, and the filter cake was washed with EtOAc. The combined filtrates were concentrated under reduced pressure. The residue was dissolved in DCM (100 mL), washed with brine (2×100 mL), dried over Na2SO4 and concentrated under reduced. The resulting residue (2.55 g) containing the sub-title compound was used in the next step directly without further purification. LCMS calc. for C7H7INO (M+H)+: m/z=247.9. found 248.0.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 36 h
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was washed with EtOAc
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DCM (100 mL)
  7. washwashed with brine (2×100 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. additionThe resulting residue (2.55 g) containing the sub-title compound
  11. customwas used in the next step directly without further purification

Sources & evidence

ORD record
ord-c021a5aad354430ea6ff862a8e40b3f7
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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