Potassium Iodide → AR-H047108

HRID 2184306Notes

Reaction equation

HRID 2184306 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([C:8]([NH2:10])=[O:9])[CH:7]=1.[CH2:16]([C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20]Cl)[CH3:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CO.C(Cl)Cl.CC(C)=O>[CH3:14][C:12]1[N:13]=[C:3]2[C:2]([NH:1][CH2:20][C:19]3[C:22]([CH3:26])=[CH:23][CH:24]=[CH:25][C:18]=3[CH2:16][CH3:17])=[CH:7][C:6]([C:8]([NH2:10])=[O:9])=[CH:5][N:4]2[C:11]=1[CH3:15]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 98557898-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamideHCID 121489182-Ethyl-6-methylbenzyl chloride2×

Product 1

HCID 9864291AR-H047108Yield 51.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide (3.3 g, 16.2 mmol), 2-ethyl-6-methylbenzylchloride (2.73 g, 16.2 mmol), potassium carbonate (8.0 g, 58 mmol) and potassium iodide (1.1 g, 6.6 mmol) were added to acetone (150 ml) and refluxed for 20 h. An additional amount of 2-ethyl-6-methylbenzylchloride (1.0 g, 5.9 mmol) was added and the reaction mixture was refluxed for 7 h. Methylene chloride (60 ml) and methanol (30 ml) were added. The reaction mixture was filtered and the solvents were evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride: methanol (100:7) as eluent. Crystallization from ethyl acetate gave 2.8 g (50%) of the title compound. 1H-NMR (300 MHz, CDCl3): δ 1.2 (t, 3H), 2.34 (s, 3H), 2.36 (s, 3H), 2.38 (s, 3H), 2.7 (q, 2H), 4.4 (d, 2H), 4.9 (bs, 1H), 6.0 (bs, 2H), 6.45 (s, 1H), 2H), 6.45 (s, 1H), 7.0-7.2 (m, 3H), 7.9, (s, 1H).

Workup

  1. temperaturerefluxed for 20 h
  2. temperaturethe reaction mixture was refluxed for 7 h
  3. filtrationThe reaction mixture was filtered
  4. customthe solvents were evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9fe6a43339074088ab99cd0be347e72f
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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