Sodium hydride → 8-(2-Chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

HRID 4306

Reaction equation

HRID 4306 reaction equation
[H-].[Na+].[I-].[Cl:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][N+](C)(C)C)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1>C(O)C#C>[Cl:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][O:8][CH2:7][C:6]#[CH:5])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 138259378-(2-Chlorobenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide

Product 1

HCID 138259178-(2-Chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridineYield 124.6%

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

To a solution of sodium hydride (60% in mineral oil dispersion, 0.186 g) in 2-propynyl alcohol (8 ml) was added 8-(2-chlorobenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (2 g) and the mixture was heated at 90°-95° C. with stirring for 1 hour. After being cooled, the mixture was poured into ice-water and the resulting precipitate was collected by filtration and dissolved in methylene chloride. The solution was treated successively with silica gel (1 g) and activated charcoal and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of methylene chloride and n-hexane to give 8-(2-chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (0.9 g).

Workup

  1. temperaturethe mixture was heated at 90°-95° C.
  2. temperatureAfter being cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutiondissolved in methylene chloride
  5. additionThe solution was treated successively with silica gel (1 g) and activated charcoal
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of methylene chloride and n-hexane

Sources & evidence

ORD record
ord-b00092430ac54cc19a9bd1a0f1697fff
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

Loading…