Potassium Fluoride → 8-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1377476Notes

Reaction equation

HRID 1377476 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[CH2:8]Cl)=[O:4].[OH:15][C:16]1[C:17]2[N:18]([C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=2)[CH:19]=[CH:20][CH:21]=1.[F-].[K+]>C(#N)C>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[CH2:8][O:15][C:16]1[C:17]2[N:18]([C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=2)[CH:19]=[CH:20][CH:21]=1)=[O:4]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chlorideHCID 224679492,3-Dimethylimidazo[1,2-a]pyridin-8-ol

Product 1

HCID 232872868-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 9.5 g of 2-methoxycarbonylamino-6-methylbenzyl chloride in 150 ml of dry acetonitrile is added dropwise at RT to a suspension of 7.2 g of 8-hydroxy-2,3-dimethylimidazo[1,2-a]pyridine in 130 ml of dry acetonitrile, to which 8 g of commercial potassium fluoride (50% by weight) in kieselguhr (for example Celite®) has been added. The mixture is heated at 70° C. for 9 h. After cooling to RT, the mixture is poured into 1 l of ice-water and extracted three times with ethyl acetate. The collected organic phases are washed with distilled water and dried over sodium sulfate. After stripping off the organic solvent in vacuo, the precipitating residue is filtered off, washed with a little ethyl acetate and ether and dried. After recrystallization from isopropanol, 2.2 g of the title compound of m.p. 176°-177° C. are obtained.

Workup

  1. additionhas been added
  2. temperatureAfter cooling to RT
  3. extractionextracted three times with ethyl acetate
  4. washThe collected organic phases are washed with distilled water
  5. dry with materialdried over sodium sulfate
  6. filtrationthe precipitating residue is filtered off
  7. washwashed with a little ethyl acetate and ether
  8. customdried
  9. customAfter recrystallization from isopropanol, 2.2 g of the title compound of m.p. 176°-177° C.
  10. customare obtained

Sources & evidence

ORD record
ord-05cf1de09de7446cbd84e3d36fb78660
Source dataset
uspto-grants-1997_09
Patent number
US05665730

Reaction notes

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