Dimethylformamide → 4-Iodo-2-((4-methoxybenzyl)oxy)pyridine

HRID 254410Notes

Reaction equation

HRID 254410 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.F[C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][N:20]=1>O>[I:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([O:15][CH2:14][C:13]2[CH:16]=[CH:17][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 668729534-Iodo-2-((4-methoxybenzyl)oxy)pyridineYield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, sodium hydride (60% oily, 4.93 g, 0.188 mmol) was added to a DMF (250 mL) solution of 4-methoxybenzyl alcohol (17.04 g), and stirred for 30 minutes. 2-Fluoro-4-iodopyridine (25.0 g) was added, and stirred at room temperature for 2 hours. Water was added to the reaction liquid, and extracted with diethyl ether. The organic layer was washed with saturated saline, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, then diisopropyl ether was added to the obtained residue, and the obtained solid was collected by filtration to obtain the entitled compound (26.15 g, 68%).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. additiondiisopropyl ether was added to the obtained residue
  7. filtrationthe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-a56616fc458f45a088065d0aa9288ab6
Source dataset
uspto-grants-2011_01
Patent number
US07875633B2

Reaction notes

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