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

HRID 8369
Notes
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Reaction equation

HRID 8369 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-9e3c8858286e46a0b9d74b5d94f6f030
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087757B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes