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

HRID 1824536Notes

Reaction equation

HRID 1824536 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-df93caa25d5c40d7bdb150aef54f1885
Source dataset
uspto-grants-2006_05
Patent number
US07041828B2

Reaction notes

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