2-Amino-4-methylpyridine → 2-(4'-Chloropropoxy-3'-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine hydrobromide

HRID 8371

Reaction equation

HRID 8371 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][Cl:15])=[C:7]([O:16][CH3:17])[CH:6]=1)=O.[NH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=1>C(O)C>[BrH:1].[Cl:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:18]=[C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]3[CH:2]=2)=[CH:6][C:7]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 22015629alpha-Bromo-3'-methoxy-4'-chloropropoxyacetophenone

Product 1

HCID 220155982-(4'-Chloropropoxy-3'-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine hydrobromideYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Step B (1.44 g) and 2-amino-4-picoline (0.486 g) in ethanol (6 mL) was heated at 73° C. for 1 hour. The reaction mixture was cooled to ambient temperature and evaporated to a yellow solid. The solid was stirred with 25 mL of dichloromethane for approximately 10 minutes. The mixture was filtered and the solid product collected to yield the title compound (1.3 g).

Workup

  1. customevaporated to a yellow solid
  2. filtrationThe mixture was filtered
  3. customthe solid product collected

Sources & evidence

ORD record
ord-979a976b36f74db790007f7dd4f936ca
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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