Sodium hydride → N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide

HRID 1423011Notes

Reaction equation

HRID 1423011 reaction equation
[Br:1][C:2]1[C:3]([CH2:8]Br)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=1.[H-].[Na+]>C1COCC1.[Cl-].[NH4+]>[Br:1][C:2]1[C:3]([CH2:8][NH:17][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][C:11]([F:10])=[CH:12][CH:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 715724-FluorobenzamideHCID 214410813-Bromo-2-(bromomethyl)pyridine

Product 1

HCID 67194294N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a mixture of 3-bromo-2-bromomethyl-pyridine (1.30 g, 5.18 mmol) and 4-fluoro-benzamide (725 mg, 5.21 mmol) in THF (20 mL) is added 60% sodium hydride in mineral oil (210 mg, 5.3 mmol) and the mixture is warmed at reflux. After 24 hours, the mixture is diluted with saturated aqueous ammonium chloride (25 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers are washed with brine (2×25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting using a gradient of 5-25% EtOAc in hexanes to afford N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide.

Workup

  1. temperaturethe mixture is warmed
  2. temperatureat reflux
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. washThe combined organic layers are washed with brine (2×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel chromatography
  9. washeluting

Sources & evidence

ORD record
ord-8a02188730a2453d9db6f5dc18aef464
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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