Sodium hydride → HCID 24871998, compound

HRID 659748Notes

Reaction equation

HRID 659748 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:15])=[C:9]([NH:11][C:12](=[O:14])C)[CH:10]=1)[CH3:2].[H-].[Na+].ClC1O[C:21]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([Cl:30])[CH:25]=2)=[CH:22][N:23]=1>CN(C=O)C>[Cl:30][C:26]1[CH:25]=[C:24]([C:21]2[O:14][C:12]([NH:11][C:9]3[CH:10]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[CH:6]=[CH:7][C:8]=3[CH3:15])=[N:23][CH:22]=2)[CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68443873HCID 68443873, compoundHCID 86633026HCID 86633026, compound

Product 1

HCID 24871998HCID 24871998, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of N-(5-(ethoxymethyl)-2-methylphenyl)ethanamide (344 mg, 1.66 mmol) in DMF (5 mL) was added to a suspension of NaH (133 mg, 3.32 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0° C. under an atmosphere of argon. The mixture was stirred for 1 h at room temperature and cooled to 0° C. A solution of 2-chloro-5-(2-chloropyridin-4-yl)oxazole (357 mg, 1.66 mmol) in DMF (5 mL) was added dropwise to the mixture. After 1 h at 0° C., the reaction was poured into ice water (20 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and filtered. After removal of solvent the residue was silica gel column chromatographed (CH2Cl2/Ethanol:98/2) to give 474 mg of 5-(2-chloropyridin-4-yl)-N-(5-(ethoxymethyl)-2-methylphenyl) oxazol-2-amine (83%) as a beige solide.

Workup

  1. temperaturecooled to 0° C
  2. waitAfter 1 h at 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customAfter removal of solvent the residue
  8. customchromatographed (CH2Cl2/Ethanol:98/2)

Sources & evidence

ORD record
ord-6dbe2aa358f64272bc476f941d8aed7b
Source dataset
uspto-grants-2011_12
Patent number
US08080669B2

Reaction notes

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