Water → HCID 67504974, compound

HRID 1929826Notes

Reaction equation

HRID 1929826 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[C:12](Cl)=[N:13][CH:14]=[C:15]([CH3:17])[CH:16]=1.O>CC(N(C)C)=O>[Br:10][C:11]1[C:12]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:13][CH:14]=[C:15]([CH3:17])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 2854373-Bromo-2-chloro-5-methylpyridine

Product 1

HCID 67504974HCID 67504974, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride dispersion in oil (˜70%, 0.68 g) was added in portions to a well stirred solution of phenol (1.33 g, 14 mmol) in DMA (100 mL). After stirring the mixture for 1 h at 50° C. 3-bromo-2-chloro-5-methyl-pyridine (2.68 g, 13 mmol) was added and stirring continued for 28 h at 100° C. The cooled mixture was poured into water and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1) to yield 1.4 g of the title compound as a colorless oil, 1H NMR(CDCl3): =2.27 (s, 3H), 7.12 (d, 2H), 7.19 (t, 1H), 7.39 (t, 2H), 7.76 (s, 1H), 7.88 (s, 1H).

Workup

  1. stirringstirring
  2. waitcontinued for 28 h at 100° C
  3. extractionextracted with diethyl ether
  4. dry with materialdried with Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1)

Sources & evidence

ORD record
ord-1dce13a83aba43dd844d2efe9367052e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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