Water → 2-(4-Methoxyphenyl)imidazo[1,2-a]pyridine

HRID 66015

Reaction equation

HRID 66015 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=O.O>C(O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:6]=[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]3[CH:14]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 104392-AminopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 6949632-(4-Methoxyphenyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 25.2 g. of sodium bicarbonate, 12.3 g. of 2-aminopyridine and 30 g. of α-bromo-p-methoxyacetophenone in 100 ml. of water and 550 ml. of absolute ethanol is heated at reflux temperatures for 1.5 hrs. The reaction mixture is concentrated under reduced pressure to a yellow solid, which is partitioned between chloroform and water. The organic layer is separated, dried over sodium sulfate. Removal of the chloroform in vacuo leaves the crude intermediate as a yellow solid. Recrystallization from ethanolwater give 15.2 g. of the desired material, m.p. 131-134° C.

Workup

  1. additionA mixture of 25.2 g
  2. temperatureat reflux temperatures for 1.5 hrs
  3. concentrationThe reaction mixture is concentrated under reduced pressure to a yellow solid, which
  4. customis partitioned between chloroform and water
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the chloroform in vacuo

Sources & evidence

ORD record
ord-09cb52c6912f41c58ce343688b1c7262
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Linked notes

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