Sodium hydride → HCID 86685951, compound

HRID 2277641Notes

Reaction equation

HRID 2277641 reaction equation
[H-].[Na+].[CH:3]([C:6]1[NH:7][CH:8]=[CH:9][N:10]=1)([CH3:5])[CH3:4].[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]Cl)[CH:17]=1>CN(C=O)C>[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:3]([CH3:5])[CH3:4])[CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 86685951HCID 86685951, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 0.073 g, 1.82 mmol) in DMF (3 mL) was added 2-isopropyl-1H-imidazole (0.173 g, 1.57 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, 3-bromo-5-chloromethyl-pyridine (0.25 g, 1.21 mmol) was added and the resulting suspension was heated at 60° C. overnight. The mixture was quenched with water (2 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.275 g, 81%) as a light yellow oil. MS: 280.0, 282.0 (M+H+).

Workup

  1. temperaturethe resulting suspension was heated at 60° C. overnight
  2. customThe mixture was quenched with water (2 mL)
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record
ord-06ad8650c8504c05aec2b27a5680f1b7
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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