Ethylene Glycol → (6-Fluoro-4-iodo-pyridin-3-ylmethoxy)-ethanol

HRID 1640887Notes

Reaction equation

HRID 1640887 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4]O.Br[CH2:8][C:9]1[C:10]([I:16])=[CH:11][C:12]([F:15])=[N:13][CH:14]=1.[OH2:17]>>[F:15][C:12]1[N:13]=[CH:14][C:9]([CH2:8][O:17][CH:3]([OH:6])[CH3:4])=[C:10]([I:16])[CH:11]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 24758Sodium hydrideHCID 66674459HCID 66674459, compound

Product 1

HCID 66738224(6-Fluoro-4-iodo-pyridin-3-ylmethoxy)-ethanolYield 38%

Procedure

Add sodium hydride (54 mg, 2.25 mmol) to 2.5 mL ethylene glycol at 0° C. and stir for 30 min at RT. Add 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.69 g, 2.14 mmol) and heat it to 120° C. for 30 min. Cool to RT, dilute with 70 mL of water, and extract with ether (3×50 mL). Combine organic layers, wash with saturated aqueous sodium chloride, thy over MgSO4, and remove the solvent. Purify by chromatography with diethylether to obtain the title compound (240 mg, 38%). MS (ES) m/z 296 [M+1]+.

Workup

  1. temperatureCool to RT
  2. extractionextract with ether (3×50 mL)
  3. washCombine organic layers, wash with saturated aqueous sodium chloride, thy over MgSO4
  4. customremove the solvent
  5. customPurify by chromatography with diethylether

Sources & evidence

ORD record
ord-e69731dedd3047b58557fa7173e9df4e
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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