2-Amino-4-methylpyridine → 2-(4'-Chloropropoxy-2'-methylphenyl)-7-methylimidazo[1,2-a]pyridine

HRID 1268678Notes

Reaction equation

HRID 1268678 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:7][C:6]=1[CH3:16])=O.[NH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1>C(O)C.CO.ClCCl>[Cl:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:17]=[C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]3[CH:2]=2)=[C:6]([CH3:16])[CH:7]=1

Participants

5

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 22015662alpha-Bromo-2'-methyl-4'-chloropropoxyacetophenone

Product 1

HCID 220156392-(4'-Chloropropoxy-2'-methylphenyl)-7-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of the product of Step B (6.77 g) and 2-amino-4-picoline (2.4 g) in ethanol (22 mL) was heated at 72° C. for 10 hours. The reaction mixture was cooled to ambient temperature and dissolved in methanol/dichloromethane and treated with Dowex® 550A basic resin until the pH of the mixture was 7. The resin was removed via filtration and the filtrate evaporated. The title compound was precipitated from ethyl acetate upon addition of hexanes and used without further purification.

Workup

  1. customThe resin was removed via filtration
  2. customthe filtrate evaporated
  3. customThe title compound was precipitated from ethyl acetate upon addition of hexanes
  4. customused without further purification

Sources & evidence

ORD record
ord-45970d5dd6304ddfa3c7532af790a1d2
Source dataset
uspto-grants-2007_04
Patent number
US07199117B2

Reaction notes

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