p-Chlorophenacyl bromide → 2-(4-Chlorophenyl)-6-methoxyimidazo[1,2-a]pyridine

HRID 231534Notes

Reaction equation

HRID 231534 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[CH:10]1[C:15]([C:16]([CH2:18]Br)=O)=[CH:14][CH:13]=[C:12]([Cl:20])[CH:11]=1.C(=O)(O)[O-].[Na+]>>[Cl:20][C:12]1[CH:13]=[CH:14][C:15]([C:16]2[N:9]=[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][N:7]3[CH:18]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 516892Sodium BicarbonateHCID 113209342-Amino-5-methoxypyridine

Product 1

HCID 153270032-(4-Chlorophenyl)-6-methoxyimidazo[1,2-a]pyridine

Procedure

A mixture of 1.3 g (10.5 mmol) of 5-methoxy-2-pyridinamine, 2.44 g (1eq) of α-bromo-4-chloroacetophenone and 1.76 g (2eq) of sodium bicarbonate in 20 ml of 95% strength alcohol is heated under reflux for 4 h 30 min. under argon. The mixture is evaporated to dryness and the residue taken up between CH2Cl2 and H2O, followed by washing, drying and evaporation. The product is purified by chromatography and then crystallized in ether. M.p. 148°-9° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 h 30 min. under argon
  3. customThe mixture is evaporated to dryness
  4. washby washing
  5. customdrying
  6. customevaporation
  7. customThe product is purified by chromatography
  8. customcrystallized in ether

Sources & evidence

ORD record
ord-3443b2a492934dd79041431e9c7e079b
Source dataset
uspto-grants-1989_07
Patent number
US04847263

Reaction notes

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