4-Methoxybenzyl alcohol → HCID 58128526, compound

HRID 1798815Notes

Reaction equation

HRID 1798815 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].F[C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][N:15]=1>CN(C=O)C>[I:20][C:17]1[CH:18]=[CH:19][C:14]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 27831792-Fluoro-5-iodopyridine

Product 1

HCID 58128526HCID 58128526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4-Methoxybenzyl alcohol (6.51 g, 47.1 mole) in 15 mL DMF was added to a stirring suspension of sodium hydride (1.973 g, 49.3 mmol) in DMF at 0° C. After 10 minutes a solution of 2-fluoro-5-iodopyridine (10 g, 44.8 mmol) in 15 mL DMF was added dropwise using an addition funnel. The reaction slowly reached room temperature, and was allowed to stir for 18 hours. The homogenous yellow solution was cooled again and quenched with about 50 ml of water. The suspension was then partitioned between ethyl acetate (200 mL) and water (150 mL). The aqueous was extracted a second time with ethyl acetate and the combined organic layers were washed with water three times and with brine twice. The organic layer was dried over sodium sulfate, filtered and evaporated. When the evaporation neared completion a white solid precipitated. Triturated with the addition of hexanes. The solid was filtered and dried on the filter. Repeated partial evaporation trituration and filtration of the resulting white solids gave the title compound.

Workup

  1. customThe reaction slowly reached room temperature
  2. temperatureThe homogenous yellow solution was cooled again
  3. customquenched with about 50 ml of water
  4. customThe suspension was then partitioned between ethyl acetate (200 mL) and water (150 mL)
  5. extractionThe aqueous was extracted a second time with ethyl acetate
  6. washthe combined organic layers were washed with water three times and with brine twice
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customWhen the evaporation
  11. customprecipitated
  12. customTriturated with the addition of hexanes
  13. filtrationThe solid was filtered
  14. customdried on the filter
  15. filtrationevaporation trituration and filtration of the resulting white solids

Sources & evidence

ORD record
ord-b371ea6f0fa04afebf99a40aabdd581f
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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