Sodium ethoxide → HCID 45254925, compound

HRID 1887475Notes

Reaction equation

HRID 1887475 reaction equation
Br[C:2]1[N:7]2[C:8]([NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[O-:25][CH2:26][CH3:27].[Na+]>>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:25][CH2:26][CH3:27])[N:7]2[C:8]=1[NH:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 45254538HCID 45254538, compound

Product 1

HCID 45254925HCID 45254925, compound

Procedure

5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine 42 (152 mg, 0.376 mmol) was added to sodium ethoxide [generated in situ by addition of sodium metal (17.32 mg) to absolute ethanol (10 ml)]. The mixture was heated under reflux for 8 h. Excess solvent was removed in vacuo and the resultant mixture was treated with water before been extracted into ethyl acetate, dried over magnesium sulphate and filtered. Excess solvent was removed under reduced pressure to give an oil that was purified by column chromatography, eluting with hexane:ethyl acetate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 h
  3. customExcess solvent was removed in vacuo
  4. additionthe resultant mixture was treated with water
  5. extractionbefore been extracted into ethyl acetate
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customExcess solvent was removed under reduced pressure
  9. customto give an oil that
  10. customwas purified by column chromatography
  11. washeluting with hexane

Sources & evidence

ORD record
ord-87ab21200b5e4e7e8463eb3ed6ec40ef
Source dataset
uspto-grants-2013_08
Patent number
US08501767B2

Reaction notes

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