Sodium hydride → HCID 59463258, compound

HRID 1712916Notes

Reaction equation

HRID 1712916 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[N:8][CH:9]=1.Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>CN(C=O)C>[Br:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]([CH2:10][O:11][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 59463258HCID 59463258, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (1.12 g, 28.0 mmol) in DMF (75 mL) was added a solution of (5-bromopyridin-3-yl)methanol (4.21 g, 22.4 mmol) in DMF (8 mL) at 0° C. The mixture was allowed to stir at 0° C. for 15 min and then 1-(chloromethyl)-4-methoxybenzene (5.41 g, 34.6 mmol) was added followed by tetra-N-butylammonium iodide (0.91 g, 2.4 mmol). The reaction mixture was allowed to vigorously stir and warm to rt overnight. The reaction mixture was partitioned between EtOAc and water. The aqueous solution was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-bromo-5-{[(4-methoxybenzyl)oxy]methyl}pyridine (4.40 g, 64%) as a yellow oil. LCMS: (FA) ES+ 308.1.

Workup

  1. stirringto vigorously stir
  2. temperaturewarm to rt overnight
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. extractionThe aqueous solution was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a78683f087a74b38ac7923e95b020239
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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