2-Amino-4-methylpyridine → 2-[3-(3-Chloro-propoxy)-phenyl]-7-methyl-imidazo[1,2-a]pyridine

HRID 8359

Reaction equation

HRID 8359 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][Cl:15])[CH:6]=1)=O.[NH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][N:18]=1>C(O)C>[Cl:15][CH2:14][CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]([C:3]2[N:16]=[C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][N:18]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 220155922-Bromo-1-[3-(3-chloro-propoxy)-phenyl]-ethanone

Product 1

HCID 220156092-[3-(3-Chloro-propoxy)-phenyl]-7-methyl-imidazo[1,2-a]pyridineYield 48.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Step B (2.6 g) and 2-amino-4-picoline (0.96 g) in ethanol (10 mL) was heated at 73° C. for 2 hours. The reaction mixture was cooled to ambient temperature and the solvent evaporated in vacuo. The residue was dissolved in dichloromethane (75 mL), washed with saturated sodium bicarbonate solution (2×75 mL), brine (75 mL), dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (ethyl acetate/hexane) to give the title compound (1.3 g).

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (75 mL)
  3. washwashed with saturated sodium bicarbonate solution (2×75 mL), brine (75 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified via silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-47a419c279bd4298997bf49bc82a7f5a
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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