Imidazo(4,5-b)pyridine → 6-Chloro-2-(4-chlorophenyl)-8-methoxyimidazo[1,2-a]-pyridine

HRID 231533

Reaction equation

HRID 231533 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C2C=CC=NC=2N=C1.[CH3:28][O-:29].[Na+].[Na]>CN(P(N(C)C)(N(C)C)=O)C.O.CO>[Cl:8][C:6]1[CH:7]=[C:2]([O:29][CH3:28])[C:3]2[N:4]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[N:11]=2)[CH:5]=1

Participants

8

Reactant 4

HCID 67504Imidazo(4,5-b)pyridineHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 142349178-Bromo-6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 142349236-Chloro-2-(4-chlorophenyl)-8-methoxyimidazo[1,2-a]-pyridine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

10 g (29.4 mmol) of 8-bromo-6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, the preparation of which compound is described in the patent application filed this day entitled: Derives d'imidazopyridines, leur preparation et leur application en therapeutique (Imidazopyridine derivatives, their preparation and their application in therapy) by the Applicant, dissolved in 60 ml of hexamethylphosphorotriamide, are added to a solution of sodium methylate prepared using 2.03 g of sodium and 15 ml of methanol, the reaction mixture is brought to 60° C. for 2 h 30 min., water is added, the mixture is extracted with CH2Cl2, the organic phase is washed with water, dried over MgSO4 and filtered, and the filtrate is concentrated under reduced pressure. The evaporation residue is recrystallized in an ethyl acetate/hexane mixture. M.p. 150°-151° C.

Workup

  1. waitfiled this day
  2. customprepared
  3. extractionthe mixture is extracted with CH2Cl2
  4. washthe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe evaporation residue is recrystallized in an ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-036eebe4c5f849078205be171443b810
Source dataset
uspto-grants-1989_07
Patent number
US04847263

Linked notes

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