Water → 6-Iodo-2-[(4-methoxybenzyl)oxy]-3-propoxypyridine

HRID 70547Notes

Reaction equation

HRID 70547 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+].Br[C:14]1[C:19]([O:20][CH2:21][CH2:22][CH3:23])=[CH:18][CH:17]=[C:16]([I:24])[N:15]=1.O>CN(C)C=O>[I:24][C:16]1[N:15]=[C:14]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:19]([O:20][CH2:21][CH2:22][CH3:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 866580042-Bromo-6-iodo-3-propoxypyridine

Product 1

HCID 867626756-Iodo-2-[(4-methoxybenzyl)oxy]-3-propoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Methoxybenzyl alcohol (689 mg) was added to a solution of sodium hydride (200 mg) in N,N-dimethylformamide (4 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 minutes. A solution of 2-bromo-6-iodo-3-propoxypyridine in N,N-dimethylformamide (2 mL) was added thereto, and the mixture was stirred at 85° C. for six hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1) to give the title compound as a colorless powder (670 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 85° C. for six hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1)

Sources & evidence

ORD record
ord-d4b187ce6d2a4eecb54c85e2e8d68c2f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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