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

HRID 1824498Notes

Reaction equation

HRID 1824498 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[F:16])=O.[NH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1>C(O)C>[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]([F:16])[CH:7]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 22015593alpha-Bromo-2'-fluoro-4'-chloropropoxyacetophenone

Product 1

HCID 220156172-(4'-Chloropropoxy-2'fluorophenyl)-7-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Step B (1.0 g) and 2-amino-4-picoline (0.357 g) in ethanol (4 mL) was heated at 73° C. for 18 hours. The reaction mixture was cooled to ambient temperature and the solvent evaporated in vacuo. A portion of the residue was purified via silica gel chromatography (ethyl acetate/hexane) directly. The remainder of the residue was dissolved in methanol/dichloromethane and treated with Dowex® 550A basic resin (Aldrich, Milwaukee, Wis.) for 10 minutes. The resin was removed via filtration and the filtrate evaporated prior to silica gel chromatography (ethyl acetate/hexane). The combined material (0.42 g) containing the title compound was used without further purification.

Workup

  1. customthe solvent evaporated in vacuo
  2. customA portion of the residue was purified via silica gel chromatography (ethyl acetate/hexane) directly
  3. dissolutionThe remainder of the residue was dissolved in methanol/dichloromethane
  4. additiontreated with Dowex® 550A basic resin (Aldrich, Milwaukee, Wis.) for 10 minutes
  5. customThe resin was removed via filtration
  6. customthe filtrate evaporated
  7. additionThe combined material (0.42 g) containing the title compound
  8. customwas used without further purification

Sources & evidence

ORD record
ord-99c760fa315447bca4a73ee4177d4c84
Source dataset
uspto-grants-2006_05
Patent number
US07041827B2

Reaction notes

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