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Methyl iodide → 2-(3-Bromophenoxy)-3-[3-(3-methoxypyridin-4-yl)propoxy]pyridine

HRID 1841562
Notes
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Reaction equation

HRID 1841562 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[OH:24])=[CH:12][CH:11]=[CH:10][N:9]=1.CI.[C:30](OCC)(=O)C>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[O:24][CH3:30])=[CH:12][CH:11]=[CH:10][N:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 99528632-(3-Bromophenoxy)-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine

Product 1

HCID 235062802-(3-Bromophenoxy)-3-[3-(3-methoxypyridin-4-yl)propoxy]pyridine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Sodium hydride (60% in mineral oil, 0.26 g, 6.5 mmol) is suspended in DMF (30 ml), and thereto is added 2-(3-bromophenoxy)-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine (2.0 g, 5.0 mmol) obtained in Example 32 at room temperature, and the mixture is stirred for 30 minutes. To the mixture is added methyl iodide (0.78 g, 0.34 mmol) under ice-cooling, and the mixture is further stirred for 30 minutes. To the reaction solution is added ethyl acetate (250 ml), and the organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by basic silica gel column chromatography (eluent: chloroform/ethyl acetate), and recrystallized from diethyl ether to give the title compound (0.75 g) as colorless crystals, m.p. 134-136° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is further stirred for 30 minutes
  3. washthe organic layer is washed with a saturated brine (50 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by basic silica gel column chromatography (eluent: chloroform/ethyl acetate)
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-7fbb5690e7ea47ef9e70c64199b936ce
Source dataset
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06683186B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes