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

HRID 1267957
Notes
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Reaction equation

HRID 1267957 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-d7cdb3c38d454145b4c4221653a430d5
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06555557B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes