Water → 5-(5-Chloropentyl)imidazo[1,2-a]pyridine

HRID 357002Notes

Reaction equation

HRID 357002 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[N:15]2[CH:16]=[CH:17][N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][Cl:24].O>O1CCCC1>[Cl:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:9][C:10]1[N:15]2[CH:16]=[CH:17][N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 813641-Bromo-4-chlorobutaneHCID 1367405-Methylimidazo[1,2-a]pyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 189366765-(5-Chloropentyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere, 51.5 ml (103 mmol) of a 2M lithium diisopropylamide solution (produced by Aldrich Company) was added to a solution of 13.6 g (103 mmol) of 5-metylimidazo[1,2-a]pyridine in 100 ml of tetrahydrofuran at -78° C. After stirring at constant temperature for 15 minutes, 17.64 g (103 mmol) of 1-bromo-4-chlorobutane was added, followed by stirring for 1 more hour. After stirring at 0° C. for 1 hour, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent; ethyl acetate) to yield 18.74 g (81.7%, light yellow oily substance) of the desired product.

Workup

  1. stirringby stirring for 1 more hour
  2. stirringAfter stirring at 0° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. distillationafter which the solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-e63b22186cb54adb957d5ea78c086ce9
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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